Name: 928-95-0|trans-2-Hexen-1-ol|95%
Brand: Ambeed
SKU: A282580
Price: 6.0 USD
Availability: InStock
Rating: 95 (35 reviews)

1
[ 6728-26-3 ]
[ 928-95-0 ]

Yield	Reaction Conditions	Operation in experiment
93%	With bis(cyclopentadienyl)dihydrozirconium In isopropyl alcohol at 130℃; for 8h;
93%	With phosphotungstic acid; sodium tetrahydroborate In methanol
92%	With isopropyl alcohol for 6h; Heating;

92%	With isopropyl alcohol for 6h; Heating;
71%	With diisobutylaluminium hydride In hexane; dichloromethane at 0℃; for 1h; Inert atmosphere;
62%	With methanol; sodium tetrahydroborate at 0 - 20℃; for 0.5h;
	With sodium tetrahydroborate In methanol; dichloromethane at -78℃; Competition with ..(aldehydes 1a, 1b, 1c, 1d).. and ..(ketones 3a, 3d, 3e, 3f,).. and ..(enones 4a, 4f).. Studies on the chemoselective reduction of various types of aldehydes and ketones with sodium borohydride.;
	With isopropyl alcohol for 6h; Heating;
	With lithium aluminium tetrahydride
100 % Chromat.	With (1,4-diazabicyclo{2.2.2}-octane)zinc(II) tetrahydoborate In tetrahydrofuran for 1.7h; Heating;
	With N-tert-butylaminoborane In tetrahydrofuran; water at 10 - 15℃; Yield given;
	With sodium hydroxide; sodium tetrahydroborate; zinc 2-ethylhexanoate 1.) THF, reflux, 2.) 40 deg, 1 h; Yield given; Multistep reaction;
		C.1 trans-2-Hexenol (Meerwein-Ponndorf-Verley reduction) Comparative Example 1 trans-2-Hexenol (Meerwein-Ponndorf-Verley reduction) In a round-bottomed flask provided with magnetic stirrer and reflux condenser, 0.5 g (5.1 mmol) of trans-2-hexenal, 12 g of isopropyl alcohol and 3.9 g of catalyst were heated under reflux. After the end of the reaction time, the reaction mixture was analyzed by gas chromatography and the yield was determined. The results are summarized in Table 1 below:
	With 2,3,4,5,6-pentahydroxy-hexanal; Bacillus subtilis glucose dehydrogenase; Saccharomyces cerevisiae dehydrogenase Gre₂p; NADPH; magnesium chloride at 30℃; aq. buffer; Enzymatic reaction;
	With D-glucose; D-glucose dehydrogenase; a putative aldehyde reductase (OsAR) from Oceanospirillum sp.MED₉₂; NADPH In aq. phosphate buffer at 25℃; for 18h; Enzymatic reaction; chemoselective reaction;	2.7. Selective reduction of aldehydes General procedure: The bioreduction of 4-acetylbenzaldehyde was carried out as follows: d-Glucose (280 mg), d-glucose dehydrogenase (11 U), NADPH (10 mg), QsAR (40 U) and 4-acetylbenzaldehyde (50 mg) were mixed in sodium phosphate buffer (25 ml, 100 mM, pH 6.5). The mixture was stirred at 25 °C for 18 h. The mixture was extracted with methyl tert-butyl ether. The organic extract was dried over anhydrous sodium sulfate and removal of the solvent gave product, 4-acetylbenzyl alcohol (38.2 mg, 76.4% yield). 1H NMR (CDCl3), δ: 2.58 (d, 3H), 4.76 (s, 2H,), 7.44(d, 2H, 2JH-H = 7.2 Hz,), 7.93 (d, 2H, 2JH-H = 7.2 Hz)). The bioreductions of hexanal and 2-nonanone were as follows: d-Glucose (36 mg), d-glucose dehydrogenase (2 U), NADPH (1.0 mg), QsAR (4 U), hexanal (10 mM) and 2-nonanone (10 mM) were mixed in sodium phosphate buffer (2 ml, 100 mM, pH 6.5). The mixture was stirred at 25 °C for 12 h. The mixture was extracted with methyl tert-butyl ether. The products were identified by comparison with authentic samples in an Agilent 7890 gas chromatography with Gamma DEXTM 225 capillary column (30 m × 0.25 mm × 0.25 mm, SUPELCO, Japan). The column temperature was controlled as follows: 50 °C for 5 min; 30 °C/min to 80 °C; 80 °C for 5 min; 20 °C/min to 100 °C; 100 °C for 8 min. The retention times for hexanal and hexanol were 6.99 and 8.66 min; 16.08 and 16.44 min for 2-nonanone and 2-nonanol, respectively.
	With hydrogen In hexane at 50℃; for 18h; Autoclave; chemoselective reaction;
	With aldehyde reductase; nicotinamide adenine dinucleotide phosphate Enzymatic reaction;
	With hydrogen In neat (no solvent) at 90℃; for 36h; chemoselective reaction;
	With potassium formate In water; N,N-dimethyl-formamide at 100℃; for 5h; Inert atmosphere; chemoselective reaction;
	With hydrogen In isopropyl alcohol at 70℃; for 2h; Autoclave; chemoselective reaction;
	With sodium tetrahydroborate In ethanol at 0℃; for 0.5h;
	With hydrogen; C₂₇H₄₁IrN₃P In 2-methyltetrahydrofuran at 25℃; for 24h; Inert atmosphere; Glovebox; chemoselective reaction;
	With hydrogen In water at 100℃; for 8h; Autoclave;
	With sodium formate; 5Ru⁽²⁺⁾5Cl^(1-)K⁽¹⁺⁾5C₂H₈N₂5C₁₀H₁₄*P₂W₁₈O₆₂^(6-) In water at 110℃; for 4h; Autoclave; Inert atmosphere;	2.4. A typical procedure for the catalytic reaction General procedure: Transfer hydrogenation reaction of ML was carried out with magneticstirring in a 50 ml stainless steel autoclave containing 5 mL 0.2 MML aqueous solution, 10 mg catalyst, and 3 mmol HCOONa was used ineach run of the reaction. The reactor was flushed thrice with 0.5 MPa N2and then 1.0 MPa N2 was flushed in the autoclave and placed in anelectric stove maintained at the reaction temperature. The reaction wasstopped at a selected time by cooling the reactor in an ice water bath. The liquid products were qualitatively analyzed by an Agilent 6890/5973 GC-MS system equipped with an HP-5MS column (30 m × 0.25mm × 0.25 m) and a flame ionization detector (FID). For quantitativemeasurements, analysis was performed on a GC128 (INESA AnalyticalInstrument Co., Ltd) gas chromatograph equipped with an FFAP capillarycolumn (30 m × 0.25 mm × 0.25 m), and 1,4-dioxane was used asthe internal standard. The conversion of ML was calculated according tothe following equation:Conversion (%) =amount of ML converted (mol)the total amount of ML (mol)×100The selectivity of GVL was normally higher than 99% without specialinstructions. For the transfer hydrogenation reaction with other substratemolecules, a similar procedure has been employed unless indicatedotherwise.

Reference： [1]Nakano, Tatsuya; Umano, Shigetoshi; Kino, Yoshio; Ishii, Yasutaka; Ogawa, Masaya [Journal of Organic Chemistry, 1988, vol. 53, # 16, p. 3752 - 3757]
[2]Heydari, Akbar; Khaksar, Samad; Akbari, Jafar; Esfandyari, Maryam; Pourayoubi, Mehrdad; Tajbakhsh, Mahmoud [Tetrahedron Letters, 2007, vol. 48, # 7, p. 1135 - 1138]
[3]Shibagaki, Makoto; Takahashi, Kyoko; Matasushita, Hajime [Bulletin of the Chemical Society of Japan, 1988, vol. 61, p. 3283 - 3288]
[4]Shibagaki, Makoto; Takahashi, Kyoko; Matasushita, Hajime [Bulletin of the Chemical Society of Japan, 1988, vol. 61, p. 3283 - 3288]
[5]Ariga, Elaine Miho; Carita Correra, Thiago; Matsushima, Jullyane Emi; McIndoe, J. Scott; Moreira Ribeiro, Francisco Wanderson; Omari, Isaac; Papa Spadafora, Bruna; Rodrigues, Alessandro; Soares, Priscila Machado Arruda; Vinhato, Elisângela; de Oliveira-Silva, Diogo [Organic and Biomolecular Chemistry, 2021, vol. 19, # 25, p. 5595 - 5606]
[6]Peňaška, Tibor; Mojzes, Melinda Meyer; Filo, Juraj; Jurdáková, Helena; Mečiarová, Mária; Šebesta, Radovan [European Journal of Organic Chemistry, 2019, vol. 2019, # 2, p. 605 - 610]
[7]Ward, Dale E.; Rhee, Chung K. [Canadian Journal of Chemistry, 1989, vol. 67, p. 1206 - 1211]
[8]Inada, Kazushige; Shibagaki, Makoto; Nakanishi, Yukio; Matsushita, Hajime [Chemistry Letters, 1993, # 10, p. 1795 - 1798]
[9]Gruenanger; Grieco [Gazzetta Chimica Italiana, 1958, vol. 88, p. 296,305]
[10]Firouzabadi, Habib; Zeynizadeh, Behzad [Bulletin of the Chemical Society of Japan, 1997, vol. 70, # 1, p. 156 - 168]
[11]Lukin, Kirill A.; Yang, ChengXi; Bellettini, John R.; Narayanan; Leanna, M. Robert; Rasmussen, Michael [Synlett, 1999, # 1, p. 59 - 60]
[12]Mimoun [Journal of Organic Chemistry, 1999, vol. 64, # 7, p. 2582 - 2589]
[13]Current Patent Assignee: LONZA GROUP AG - US6075145, 2000, A
[14]Location in patent: experimental part Mueller, Marion; Katzberg, Michael; Bertau, Martin; Hummel, Werner [Organic and Biomolecular Chemistry, 2010, vol. 8, # 7, p. 1540 - 1550]
[15]Li, Guangyue; Ren, Jie; Wu, Qiaqing; Feng, Jinhui; Zhu, Dunming; Ma, Yanhe [Journal of Molecular Catalysis B: Enzymatic, 2013, vol. 90, p. 17 - 22]
[16]Cano, Israel; Huertos, Miguel A.; Chapman, Andrew M.; Buntkowsky, Gerd; Gutmann, Torsten; Groszewicz, Pedro B.; Van Leeuwen, Piet W. N. M. [Journal of the American Chemical Society, 2015, vol. 137, # 24, p. 7718 - 7727]
[17]Kunishima, Mikiko; Yamauchi, Yasuo; Mizutani, Masaharu; Kuse, Masaki; Takikawa, Hirosato; Sugimoto, Yukihiro [Journal of Biological Chemistry, 2016, vol. 291, # 27, p. 14023 - 14033]
[18]Ye, Tian-Nan; Li, Jiang; Kitano, Masaaki; Sasase, Masato; Hosono, Hideo [Chemical Science, 2016, vol. 7, # 9, p. 5969 - 5975]
[19]Gao, Yanxiu; Wang, Jie; Han, Aijuan; Jaenicke, Stephan; Chuah, Gaik Khuan [Catalysis science and technology, 2016, vol. 6, # 11, p. 3806 - 3813]
[20]Hu, Duo; Fan, Wenqian; Liu, Zhi; Li, Ling [ChemCatChem, 2018, vol. 10, # 4, p. 779 - 788]
[21]Colella, Marco; Tota, Arianna; Großjohann, Angela; Carlucci, Claudia; Aramini, Andrea; Sheikh, Nadeem S.; Degennaro, Leonardo; Luisi, Renzo [Chemical Communications, 2019, vol. 55, # 58, p. 8430 - 8433]
[22]Álvarez, Eleuterio; Hernández-Juárez, Martín; López-Serrano, Joaquín; Paneque, Margarita; Rendón, Nuria; Sánchez, Práxedes; Suárez, Andrés [Organometallics, 2021, vol. 40, # 9, p. 1314 - 1327]
[23]Chen, Manyu; Xia, Jie; Li, Huan; Zhao, Xiuge; Peng, Qingpo; Wang, Jiajia; Gong, Honghui; Dai, Sheng; An, Pengfei; Wang, Haifeng; Hou, Zhenshan [ChemCatChem, 2021, vol. 13, # 17, p. 3801 - 3814]
[24]Chen, Manyu; Cui, Kai; Hou, Zhenshan; Peng, Qingpo; Wang, Jiajia; Wei, Xinjia; Zhao, Xiuge [Molecular catalysis, 2022, vol. 517]

2
[ 27829-72-7 ]
[ 928-95-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 5915 - 5918
[2]Chemistry of Natural Compounds,2000,vol. 36,p. 623 - 624
[3]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1957,vol. 308,p. 277,282
[4]Chemistry - A European Journal,2012,vol. 18,p. 11880 - 11883

3
[ 928-95-0 ]
[ 73881-10-4 ]

Yield	Reaction Conditions	Operation in experiment
96%	With tetrabutylammomium bromide; (chloro-phenylthio-methylene)dimethylammonium chloride In dichloromethane at 20℃;
90%	With phosphorus tribromide In diethyl ether
89%	With phosphorus tribromide In dichloromethane at 25℃; for 3h; Inert atmosphere;	5.2.1. (E)-1-(2-Tetrahydropyranyl)oxy-nona-5-en-2-yne (3) To a solution of 10.0 g (0.1 mol) of E-2-hexen-1-ol (2) in 100 mL of dichloromethane at -10 °C under argon, was added 13.5 g (0.05 mol) of PBr3. After stirring at 25 °C for 3 h, the reaction solution was washed with a saturated aqueous solution of NaHCO3 (50 mL), water, and brine, dried (MgSO4), concentrated to give 14.5 g (89% yield) of E-1-bromo-2-hexene, which was used in the following step without purification. 1H NMR δ 5.8-5.65 (m, 2H, CH), 3.96 (d, J = 7 Hz, 2H), 2.05 (q, J = 7 Hz, 2H), 1.41 (sextet, J = 7 Hz, 2H), 0.91 (t, J = 7 Hz, 3H); 13C NMR δ 136.7, 126.7, 34.3, 33.9, 22.2, 13.8; MS (electrospray) m/z 165.1 and 163.1 (M + H+; 100%; bromine isotopes).

81%	With pyridine; triphenyl phosphite; bromine In diethyl ether Ambient temperature;
77%	With phosphorus tribromide In diethyl ether at 0 - 20℃; for 18h;
47%	With phosphorus tribromide In diethyl ether at 0 - 20℃; for 0.833333h;
	With phosphorus tribromide; Petroleum ether at -15 - 20℃;
	With phosphorus tribromide In Petroleum ether
	With bromine; triphenylphosphine In acetonitrile
	With hydrogen bromide
	With phosphorus tribromide In diethyl ether at -30 - 20℃; for 1h; Inert atmosphere;
	With phosphorus tribromide In diethyl ether at 0℃; for 1h;
	With phosphorus tribromide In diethyl ether at 0 - 20℃; for 1.5h;
	With phosphorus tribromide In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere;
	With phosphorus tribromide In diethyl ether at 0℃; Darkness; Inert atmosphere;
	With phosphorus tribromide In diethyl ether; dichloromethane at 0℃; for 2h;
	With phosphorus tribromide In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;
	With phosphorus tribromide In dichloromethane at 0℃; for 0.5h; Inert atmosphere;	4.4.2. Synthesis of Horner Reagent for Olefination The synthesis of dimethyl (E)-hex-2-en-1-ylphosphonate (S8) was commenced with(E)-hex-2-en-1-ol (S6). (E)-hex-2-en-1-ol (S6) (1.0 g, 7.5 mmol). It was added into CH2Cl2 and then PBr3 (3.1 g, 11.3 mmol) was added slowly at 0 °C. The mixture was stirred for 30 min before adding the saturated NaHCO3 solution (10 mL). It was extracted with EtOAc and the combination of organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo to obtain the crude (E)-1-bromohex-2-ene (S7, 875.9 mg). The mixture of S7 (875.9 mg, 5.4 mmol) and P(OCH3)3 was heated to 130 °C for 4 h, followed by evaporation for the low boiling point impurities. The mixture was purified by flash chromatography (PE/EtOAc = 4:1) afforded S8 (761.7 mg, 74% yield).

Reference： [1]Gomez; Gellibert; Wagner; Mioskowski [Tetrahedron Letters, 2000, vol. 41, # 32, p. 6049 - 6052]
[2]Morisaki; Funabashi; Furukawa; Shimazawa; Kanematsu; Ando; Okuda; Iwasaki [Chemical and Pharmaceutical Bulletin, 1992, vol. 40, # 11, p. 2945 - 2953]
[3]Location in patent: experimental part Kim, Yunjeong; George, David; Prior, Allan M.; Prasain, Keshar; Hao, Shuanghong; Le, Duy D.; Hua, Duy H.; Chang, Kyeong-Ok [European Journal of Medicinal Chemistry, 2012, vol. 50, p. 311 - 318]
[4]Mancini, Ines; Guella, Graziano; Pietra, Francesco [Helvetica Chimica Acta, 1991, vol. 74, # 5, p. 941 - 950]
[5]Race, Nicholas J.; Bower, John F. [Organic Letters, 2013, vol. 15, # 17, p. 4616 - 4619]
[6]Saito, Hiroki; Kato, Ranmaru; Ikeuchi, Kazutada; Suzuki, Takahiro; Tanino, Keiji [Organic Letters, 2021, vol. 23, # 24, p. 9606 - 9610]
[7]Truscheit,R.; Eiter,K. [Justus Liebigs Annalen der Chemie, 1962, vol. 658, p. 65 - 90] Yoshioka [Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1958, vol. 78, p. 258][Chem.Abstr., 1958, p. 11740]
[8]Truscheit,R.; Eiter,K. [Justus Liebigs Annalen der Chemie, 1962, vol. 658, p. 65 - 90]
[9]Ando; Vu; Yoshida; Takahashi [Agricultural and Biological Chemistry, 1982, vol. 46, # 3, p. 717 - 722]
[10]Ho; Tao; Tsai; Wu; Tseng; Chow [Journal of Chemical Ecology, 1996, vol. 22, # 2, p. 271 - 285]
[11]Sakanishi, Kohei; Itoh, Shunya; Sugiyama, Ryosuke; Nishimura, Shinichi; Kakeya, Hideaki; Iwabuchi, Yoshiharu; Kanoh, Naoki [European Journal of Organic Chemistry, 2014, vol. 2014, # 7, p. 1376 - 1380]
[12]Tayama, Eiji; Naganuma, Noriko; Iwamoto, Hajime; Hasegawa, Eietsu [Chemical Communications, 2014, vol. 50, # 52, p. 6860 - 6862]
[13]Wang, Haoxuan; Yang, Jeffrey C.; Buchwald, Stephen L. [Journal of the American Chemical Society, 2017, vol. 139, # 25, p. 8428 - 8431]
[14]Li, Zhong-Yuan; Lakmal, Hetti Handi Chaminda; Qian, Xiaolin; Zhu, Zhenyu; Donnadieu, Bruno; McClain, Sarah J.; Xu, Xue; Cui, Xin [Journal of the American Chemical Society, 2019, vol. 141, # 40, p. 15730 - 15736]
[15]Liu, Feng; Liu, Jia-Li; tu, Jia-Lin [Organic Letters, 2020, vol. 22, # 18, p. 7369 - 7372]
[16]Kim, Hanbyul; Jang, Jiwon; Shin, Seunghoon [Journal of the American Chemical Society, 2020, vol. 142, # 49, p. 20788 - 20795]
[17]Lee, Sang M.; Cheng, Qiang; Yu, Xueliang; Liu, Shuai; Johnson, Lindsay T.; Siegwart, Daniel J. [Angewandte Chemie - International Edition, 2021, vol. 60, # 11, p. 5848 - 5853][Angew. Chem., 2021, vol. 133, # 11, p. 5912 - 5917,6]
[18]Xiao, Hong-Xiu; Yan, Qing-Xiang; He, Zhi-Hui; Zou, Zheng-Biao; Le, Qing-Qing; Chen, Ting-Ting; Cai, Bing; Yang, Xian-Wen; Luo, Su-Lan [Marine Drugs, 2021, vol. 19, # 6]

4
[ 928-95-0 ]
[ 37658-00-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	With (chloro-phenylthio-methylene)dimethylammonium chloride In dichloromethane at 20℃; for 3h;
87%	With 1-chloro-1-(dimethylamino)-2-methyl-1-propene In chloroform-d1 at 0 - 20℃; for 1h; Inert atmosphere; regioselective reaction;	4.2. General procedure for the reaction of a-haloenamines withallylic and propargylic alcohols General procedure: Reactions were performed in an oven- or flame-dried three neckround-bottomed flask under dry argon and with magnetic stirring. The flask was equipped with a septum and a refrigerator isolated from moisture by an oil trap. A solution of alcohol in CDCl3 or CH2Cl2 was syringed in through the septum and cooled down at 0 °C. A solution of α-haloenamine (1.1 equiv.) was then syringed into the flask and the mixture was left at room temperature. The reaction was followed by 1H NMR. Yields were determined after removal of the solvent either by 1H NMR using an added standard (usually benzene or toluene) or by GLC. In some cases, the halides were purified by distillation or flash chromatography. The isolated yields were always very close to those measured by NMR or GLC. Most of the halogenation products obtained in this study were known compounds: their spectroscopic properties have been shown to be identical to those reported in the literature Therefore, no data or only 1H NMR are reported for these molecules.
66%	With N-chloro-succinimide; dimethylsulfide In dichloromethane at -20 - 0℃;

	With pyridine; thionyl chloride
	With <i>N</i>,<i>N</i>-dimethyl-aniline; phosphorus trichloride In Petroleum ether
	With N-chloro-succinimide; dimethylsulfide In dichloromethane at -20 - 0℃;

Reference： [1]Gomez; Gellibert; Wagner; Mioskowski [Tetrahedron Letters, 2000, vol. 41, # 32, p. 6049 - 6052]
[2]Munyemana, François; Patiny, Luc; Ghosez, Léon [Tetrahedron, 2021, vol. 89]
[3]Fox, Richard J.; Lalic, Gojko; Bergman, Robert G. [Journal of the American Chemical Society, 2007, vol. 129, # 46, p. 14144 - 14145]
[4]Mangold,D.J. [Diss.<Univ.Texas 1954> S.65]
[5]Elferink,J.G.R. et al. [Recueil des Travaux Chimiques des Pays-Bas, 1972, vol. 91, p. 989 - 1000]
[6]Evans, David A.; Aye, Yimon; Wu, Jimmy [Organic Letters, 2006, vol. 8, # 10, p. 2071 - 2073]

5
[ 764-60-3 ]
[ 928-95-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	With lithium aluminium tetrahydride In tetrahydrofuran for 5h; Heating;
90.5%	With lithium aluminium tetrahydride In tetrahydrofuran for 1.5h; Heating;
87%	With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether for 2h; Heating;

86%	With lithium aluminium tetrahydride
	With ammonia; sodium
	With ammonia; sodium for 1.5h;
	With lithium aluminium tetrahydride In tetrahydrofuran for 3h; Heating; Yield given;
	With hydrogen In d⁽⁴⁾-methanol at 24.84℃;

Reference： [1]Vig, O. P.; Jindal, R. T. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 9, p. 919 - 920]
[2]Nakagawa, Naoshi; Mori, Kenji [Agricultural and Biological Chemistry, 1984, vol. 48, # 10, p. 2505 - 2510]
[3]Thijs, Lambertus; Waanders, Peter P.; Stokkingreef, Edwin H. M.; Zwanenburg, Binne [Recueil des Travaux Chimiques des Pays-Bas, 1986, vol. 105, p. 332 - 337]
[4]Frankel, Edwin N.; Garwood, Robert F.; Vinson, John R.; Weedon, Basil C. L. [Journal of the Chemical Society. Perkin transactions I, 1982, # 11, p. 2707 - 2714]
[5]Mangold,D.J. [Diss.<Univ.Texas 1954>S.62]
[6]Vasil'ev, A. A.; Cherkaev, G. V.; Nikitina, M. A. [Russian Journal of Organic Chemistry, 1994, vol. 30, # 6.1, p. 870 - 875][Zhurnal Organicheskoi Khimii, 1994, vol. 30, # 6, p. 816 - 821]
[7]Tomassy, Beata; Zwierzak, Andrzej [Synthetic Communications, 1998, vol. 28, # 7, p. 1201 - 1214]
[8]Schleyer; Niessen; Bargon [New Journal of Chemistry, 2001, vol. 25, # 3, p. 423 - 426]

6
[ 928-95-0 ]
[ 75-36-5 ]
[ 2497-18-9 ]

Reference： [1]Tetrahedron,1994,vol. 50,p. 217 - 254
[2]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1957,vol. 308,p. 277,282

7
[ 928-95-0 ]
[ 16420-13-6 ]
[ 67643-79-2 ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: (E)-2-Hexen-1-ol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Stage #2: N,N-Dimethylthiocarbamoyl chloride With sodium iodide In tetrahydrofuran; mineral oil at 0 - 20℃;
	With potassium hydride In tetrahydrofuran

Reference： [1]Overman, Larry E.; Roberts, Scott W.; Sneddon, Helen F. [Organic Letters, 2008, vol. 10, # 7, p. 1485 - 1488]
[2]Overman,L.E. et al. [Journal of the American Chemical Society, 1978, vol. 100, p. 4822 - 4834]

8
[ 10439-23-3 ]
[ 928-95-0 ]
[ 106709-73-3 ]

Yield	Reaction Conditions	Operation in experiment
70%	With pyridine In tetrahydrofuran at 0℃; for 4h; Inert atmosphere;
	With pyridine In tetrahydrofuran at 0℃; for 4h; Yield given;

Reference： [1]Xu, Qing-Long; Dai, Li-Xin; You, Shu-Li [Organic Letters, 2010, vol. 12, # 4, p. 800 - 803]
[2]Hiroi, Kunio; Makino, Kunitaka [Chemical and pharmaceutical bulletin, 1988, vol. 36, # 5, p. 1727 - 1737]

9
[ 13894-63-8 ]
[ 928-95-0 ]

Yield	Reaction Conditions	Operation in experiment
	With diisobutylaluminium hydride In diethyl ether at -78℃;
	With diisobutylaluminium hydride In tetrahydrofuran at -78 - 20℃;
	With diisobutylaluminium hydride In dichloromethane at 0℃; for 1h; Inert atmosphere;

Reference： [1]Mulzer, Johann; Lammer, Ortrud [Chemische Berichte, 1986, vol. 119, # 7, p. 2178 - 2190]
[2]Anderson, Carolyn E.; Overman, Larry E.; Watson, Mary P.; Maddess, Matthew L.; Lautens, Mark [Organic Syntheses, 2005, vol. 82, p. 134 - 139]
[3]Huang, Jiaxin; Li, Jie; Yang, Wen; Zhang, Kezhuo; Zhao, Pei; Zhao, Wanxiang [Chemical Communications, 2022, vol. 58, # 2, p. 302 - 305]

10
[ 928-95-0 ]
[ 6728-26-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With oxygen In N,N-dimethyl-formamide at 25℃; for 1.75h;
100%	With manganese(IV) oxide; 3-mercapto-2-(mercaptomethyl)-ethyl propanoate; 4 A molecular sieve In dichloromethane Heating;
99%	With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃; for 16h; Inert atmosphere;

97%	With oxygen In benzene at 60℃; for 24h;
93%	With bis(cyclopentadienyl)dihydrozirconium; benzaldehyde In toluene at 110℃; for 8h;
91%	With (1,10-phenanthrolino)2-tetrapalladium(CO)(acetate)4; oxygen In benzene at 50℃; for 24h;
84%	With tert.-butylhydroperoxide In 2,2,4-trimethylpentane; dichloromethane for 12h; Ambient temperature;
84%	With 1-methyl-1H-imidazole; [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen; copper(ll) bromide In acetonitrile at 20℃; for 2h;
81%	With recombinant Pleurotus eryngii aryl alcohol oxidase; oxygen; catalase In aq. buffer at 30℃; for 18h; Flow reactor; Enzymatic reaction;	Flow reactor experiments General procedure: PFA microreactor coils (750 μm ID) with a volume of 3 and 6 mL were constructed. The reaction mixture was introducedvia a syringe pump (Fusion 200, Chemyx), while the pure oxygen flow was controlled by a mass flow controller (ELFLOW, Bronkhorst), resulting in a segmented flow (SupportingInformation File 1, Figure S8). Residence times were taken as the time between the solution entering and exiting the coil andwere varied by altering the flow, keeping the ratio of oxygen toliquid at three to one. Samples were collected on ice and assoon as enough volume was collected, extracted with ethylacetate and analysed by GC (vide infra).
80%	With mIBX In water at 20℃; for 18h;
71%	With bromine; oxygen In acetic acid at 60℃; for 6h;
66%	With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate; 5,6,9,10-tetrahydro-4H,8H-pyrido[3,2,1-ij][1,6]naphthyridine; 4,4'-Dimethoxy-2,2'-bipyridin; oxygen In acetonitrile at 147℃; for 15.5h; Schlenk technique; Inert atmosphere;
42%	With 4-(N,N-dimethylamino)pyridinium chlorochromate In dichloromethane for 16h;
91 % Chromat.	With tris(triphenylphosphine)ruthenium(II) chloride In benzene at 25℃; for 4h;
	electrochem. oxidn.;
90 % Chromat.	With tert.-butylhydroperoxide In dichloromethane; 1,2-dichloro-ethane at 20℃; for 12h;
69 % Chromat.	With pyridine; 4 A molecular sieve; oxygen In various solvent(s) at 100℃; for 1h;
90 % Chromat.	With modified o-iodoxybenzoic acid In water at 20℃; for 18h;
	With Celite; pyridinium chlorochromate In dichloromethane at 20℃; for 3h;
67 % Chromat.	With quinolinium monofluorochromate(VI) In hexane at 20℃; for 2h;
100 % Spectr.	With manganese(IV) oxide; Me₂S=CO₂Et In dichloromethane Heating;
93 % Chromat.	With CrO₃/silica gel In dichloromethane at 20℃; for 0.25h;
	With oxygen In dimethyl sulfoxide at 135℃; for 2h;
33 % Chromat.	With oxygen; chloranil; decalin In water at 90℃; for 18h;
46 % Turnov.	With 1,1,1-trifluoro-2-propanone In dichloromethane; toluene at 20℃; for 24h;
81 % Chromat.	With dihydrogen peroxide at 90℃; for 2h;
	Multi-step reaction with 2 steps 1: pyridine / diethyl ether / 5 h / 25 - 30 °C 2: 95 percent Chromat_. / Pd(OAc)2 / acetonitrile / 1 h / 80 °C / Heating
	With oxygen In α,α,α-trifluorotoluene at 110℃;
98 %Chromat.	With acetaldehyde at 30℃; for 24h; aq. phosphate buffer; Microbiological reaction; Combinatorial reaction / High throughput screening (HTS); chemoselective reaction;
	With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; N,N′-{1,3-bis[(pyridine-2-ylmethyl)amino]propan-2-al}atodicopper(II)(μ-acetato)diperchlorate; oxygen; sodium hydroxide In water; acetonitrile at 20℃;
	With tert.-butylhydroperoxide In water; acetonitrile at 60℃; for 5h;
	With dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dichloromethane at 0℃; for 1h; Inert atmosphere;
	With oxygen In α,α,α-trifluorotoluene at 110℃;	2 In the oxidation reaction of unsaturated aliphatic alcohols, the maximal oxidation rates obtained for secondary alcohols was higher than those observed for primary alcohols, as presented in Table 2. The only significant by-products in these reactions were the saturated aldehdyes or ketones, namely propanal, hexanal, butanone and so forth, and in the cases where the alcohols were pure E/Z hexen-1-ol isomers, the E-2-hexenal was the major product. No significant amounts of carboxylic acids were formed.Table 2 presents the results obtained for unsaturated alcohols under reaction conditions of 0.1 mmol alcohol, 5 μmol Pd-POM-1, 1 ml TFT, 2 bars O2, and 110° C.,wherein the rate of oxidation yields, determined by GC analysis, is shown as molar percentage, the time for completion/arrest in minutes, and the selectivity for the major product (β-unsaturated aldehyde or ketone respectively) in molar percentage. As can be seen in Table 2, the cis isomers were isomerized to trans products, to and as noticeable from the formation of saturated aldehydes and ketones as by-products, the isomerisation of the double bond competed with the alcohol oxidation reaction.
	With oxygen In toluene at 80℃; for 1h;
> 99 %Chromat.	With palladium in UiO-67; air In toluene at 80℃; for 30h; Green chemistry;
	With Arabidopsis thaliana berberine bridge enzyme-like protein 15 L₁₈₂V; oxygen In dimethyl sulfoxide at 30℃; for 24h; Enzymatic reaction;	2.4. Substrate screening General procedure: Reactions were carried out in 50 mM MES buffer pH 7.0 in the presence of 20% (v/v) DMSO. A total volume of 2 mL reaction mixture was incubated in 11 mL glass test tube with screw cap (Pyrex,Darmstadt, Germany) at 30 C in an orbital shaker at 110 rpm. The reaction was started by the addition of 10 L enzyme to achieve a final enzyme concentration of 1.2 M. After 24 h the reaction mixture was extracted with ethyl acetate (2 1 mL), the combined organic phase was dried with Na2SO4 and subjected to GC analysis to identify putative products.
	With recombinant aryl alcohol oxidase from Pleurotus eryngii; oxygen; catalase In aq. phosphate buffer; dodecane at 20℃; for 336h; Enzymatic reaction;
	With silica gel; pyridinium chlorochromate In dichloromethane for 4h; Molecular sieve; Inert atmosphere;	(E)-Hex-2-enal 6 To a suspension of PCC (0.57 g, 2.64 mmol), Celite (0.9 g), and 4 Å molecular sieves (activated powder, 0.9 g) in CH2Cl2 (15 mL) under an atmosphere of nitrogen was added a solution of 12 (0.22 g, 1.3 mmol) in CH2Cl2 (5 mL) dropwise. After stirring for 4 hours, diethyl ether (40 mL) was added and the mixture stirred for an additional hour before filtering over a Celite and silica pad. The solid was washed with 9:1 pentane:diethyl ether (60 mL) and the mixture was concentrated in vacuo without application of heat. Due to the volatility of 6, it was not isolated, solvent was concentrated in vacuo, and crude 6 was used directly in the next reaction.
	With Dess-Martin periodane In dichloromethane at 0℃; for 1h; Inert atmosphere;

Reference： [1]Semmelhack, M. F.; Schmid, Christopher R.; Cortes, David A.; Chou, Chuen S. [Journal of the American Chemical Society, 1984, vol. 106, # 11, p. 3374 - 3376]
[2]McAllister, Graeme D.; Oswald, Magalie F.; Paxton, Richard J.; Raw, Steven A.; Taylor, Richard J.K. [Tetrahedron, 2006, vol. 62, # 28, p. 6681 - 6694]
[3]Healy, Alan R.; Vinale, Francesco; Lorito, Matteo; Westwood, Nicholas J. [Organic Letters, 2015, vol. 17, # 3, p. 692 - 695]
[4]Kaneda, Kiyotomi; Fujie, Yoko; Ebitani, Kohki [Tetrahedron Letters, 1997, vol. 38, # 52, p. 9023 - 9026]
[5]Nakano, Tatsuya; Ishii, Yasutaka; Ogawa, Masaya [Journal of Organic Chemistry, 1987, vol. 52, # 22, p. 4855 - 4859]
[6]Kaneda, Kiyotomi; Fujii, Masanori; Morioka, Kengo [Journal of Organic Chemistry, 1996, vol. 61, # 14, p. 4502 - 4503]
[7]Choudary, B. M.; Durgaprasad, A.; Valli, V. L. K. [Tetrahedron Letters, 1990, vol. 31, # 40, p. 5785 - 5788]
[8]Location in patent: experimental part Kumpulainen, Esa T. T.; Koskinen, Ari M. P. [Chemistry - A European Journal, 2009, vol. 15, # 41, p. 10901 - 10911]
[9]Van Schie, Morten M.C.H.; De Almeida, Tiago Pedroso; Laudadio, Gabriele; Tieves, Florian; Fernández-Fueyo, Elena; Noël, Timothy; Arends, Isabel W.C.E.; Hollmann, Frank [Beilstein Journal of Organic Chemistry, 2018, vol. 14, p. 697 - 703]
[10]Current Patent Assignee: WESTERN ILLINOIS UNIVERSITY - US2004/30187, 2004, A1 Location in patent: Page Sheet 2
[11]Hirano, Masao; Morimoto, Takashi; Itoh, Keiko [Bulletin of the Chemical Society of Japan, 1988, vol. 61, # 10, p. 3749 - 3751]
[12]Koenning, Daniel; Hiller, Wolf; Christmann, Mathias [Organic Letters, 2012, vol. 14, # 20, p. 5258 - 5261]
[13]Guziec, Frank S.; Luzzio, Frederick A. [Journal of Organic Chemistry, 1982, vol. 47, # 9, p. 1787 - 1789]
[14]Tomioka, Hiroki; Takai, Kazuhiko; Oshima, Koichiro; Nozaki, Hitosi [Tetrahedron Letters, 1981, vol. 22, # 17, p. 1605 - 1608]
[15]Komoschinski, Joachim; Steckhan, Eberhard [Tetrahedron Letters, 1988, vol. 29, # 27, p. 3299 - 3300]
[16]Fung, Wai-Hong; Yu, Wing-Yiu; Che, Chi-Ming [Journal of Organic Chemistry, 1998, vol. 63, # 9, p. 2873 - 2877]
[17]Coleman, Karl S.; Coppe, Maurice; Thomas, Christophe; Osborn, John A. [Tetrahedron Letters, 1999, vol. 40, # 19, p. 3723 - 3726]
[18]Thottumkara, Arun P; Vinod, Thottumkara K [Tetrahedron Letters, 2002, vol. 43, # 4, p. 569 - 572]
[19]Bressette, Andrew R.; Glover IV, Louis C. [Synlett, 2004, # 4, p. 738 - 740]
[20]Rajkumar, G. Abraham; Sivamurugan; Arabindoo, Banumathi; Murugesan [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 5, p. 936 - 946]
[21]Oswald, Magalie F.; Raw, Steven A.; Taylor, Richard J. K. [Organic Letters, 2004, vol. 6, # 22, p. 3997 - 4000]
[22]Gonzalez-Nunez, Maria Elena; Mello, Rossella; Olmos, Andrea; Accrete, Rafael; Asensio, Gregorio [Journal of Organic Chemistry, 2006, vol. 71, # 3, p. 1039 - 1042]
[23]Khenkin, Alexander M.; Neumann, Ronny [Journal of Organic Chemistry, 2002, vol. 67, # 20, p. 7075 - 7079]
[24]Neumann, Ronny; Khenkin, Alexander M.; Vigdergauz, Inga [Chemistry - A European Journal, 2000, vol. 6, # 5, p. 875 - 882]
[25]Mello, Rossella; Martinez-Ferrer, Jaime; Asensio, Gregorio; Gonzalez-Nunez, Maria Elena [Journal of Organic Chemistry, 2007, vol. 72, # 24, p. 9376 - 9378]
[26]Kon, Yoshihiro; Usui, Yoko; Sato, Kazuhiko [Chemical Communications, 2007, # 42, p. 4399 - 4400]
[27]Minami, Ichiro; Tsuji, Jiro [Tetrahedron, 1987, vol. 43, # 17, p. 3903 - 3916]
[28]Location in patent: scheme or table Barats, Delina; Neumann, Ronny [Advanced Synthesis and Catalysis, 2010, vol. 352, # 2-3, p. 293 - 298]
[29]Location in patent: experimental part Orbegozo, Thomas; De Vries, Johannes G.; Kroutil, Wolfgang [European Journal of Organic Chemistry, 2010, # 18, p. 3445 - 3448]
[30]Striegler, Susanne; Dunaway, Natasha A.; Gichinga, Moses G.; Milton, Lisa K. [Tetrahedron, 2010, vol. 66, # 40, p. 7927 - 7932]
[31]Location in patent: experimental part Chattopadhyay, Tanmay; Kogiso, Masaki; Asakawa, Masumi; Shimizu, Toshimi; Aoyagi, Masaru [Catalysis Communications, 2010, vol. 12, # 1, p. 9 - 13]
[32]Location in patent: experimental part Radha Krishna, Palakodety; Ramana, D. Venkata [Journal of Organic Chemistry, 2012, vol. 77, # 1, p. 674 - 679]
[33]Current Patent Assignee: WEIZMANN INSTITUTE OF SCIENCE - US2012/197033, 2012, A1 Location in patent: Page/Page column 10-11
[34]Chen, Gongzhou; Wu, Shijian; Liu, Hongli; Jiang, Huanfeng; Li, Yingwei [Green Chemistry, 2013, vol. 15, # 1, p. 230 - 235]
[35]Chen, Liyu; Chen, Huirong; Luque, Rafael; Li, Yingwei [Chemical Science, 2014, vol. 5, # 10, p. 3708 - 3714]
[36]Pils, Sabine; Schnabl, Kordula; Wallner, Silvia; Daniel, Bastian; Macheroux, Peter; Kljajic, Marko; Kupresanin, Nina; Breinbauer, Rolf; Fuchs, Michael; Rocha, Raquel; Schrittwieser, Joerg H.; Kroutil, Wolfgang [Journal of Molecular Catalysis B: Enzymatic, 2016, vol. 133, p. S6 - S14]
[37]de Almeida; van Schie; Ma; Tieves; Younes; Fernández-Fueyo; Arends; Riul; Hollmann [Advanced Synthesis and Catalysis, 2019, vol. 361, # 11, p. 2668 - 2672]
[38]Muhl, Jennifer R.; Pilkington, Lisa I.; Deed, Rebecca C. [Tetrahedron Letters, 2020, vol. 61, # 28]
[39]Elizebath, Drishya; Jachak, Gorakhnath R.; Reddy, D. Srinivasa; Shanmugam, Dhanasekaran; Shukla, Anurag [European Journal of Organic Chemistry, 2021, vol. 2021, # 15, p. 2212 - 2218]

11
[ 928-95-0 ]
[ 115977-54-3 ]

Yield	Reaction Conditions	Operation in experiment
82%	With chloro-trimethyl-silane; water; sodium iodide In acetonitrile for 0.5h; Ambient temperature;
75%	With chloro-trimethyl-silane; water; sodium iodide In acetonitrile for 0.5h; Ambient temperature;
	With chloro-trimethyl-silane; sodium iodide In [D₃]acetonitrile at 20℃; for 0.5h;

With chloro-trimethyl-silane; iodine In acetonitrile at 20℃;

Reference： [1]Kanai, Takaya; Irifune, Shinji; Ishii, Yasutaka; Ogawa, Masaya [Synthesis, 1989, # 4, p. 283 - 286]
[2]Kanai, Takaya; Kanagawa, Yoshinori; Ishii, Yasutaka [Journal of Organic Chemistry, 1990, vol. 55, # 10, p. 3274 - 3277]
[3]Wada; Miyoshi; Nishio; Murakami; Fukuma [Bulletin of the Chemical Society of Japan, 2000, vol. 73, # 3, p. 689 - 692]
[4]Location in patent: scheme or table Morandi, Stefania; Pellati, Federica; Ori, Claudia; Adinolfi, Barbara; Nieri, Paola; Benvenuti, Stefania; Prati, Fabio [Organic and Biomolecular Chemistry, 2008, vol. 6, # 23, p. 4333 - 4339]

12
[ 928-95-0 ]
[ 106498-75-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With tert.-butylhydroperoxide In chloroform for 4h; Reflux;
100%	With tert.-butylhydroperoxide In acetonitrile at 80℃; for 24h;	Catalytic epoxidation, general procedure General procedure: All epoxidation reactions of the allyl alcohols (geraniol, cin-namyl alcohol, trans-2-hexen-1-ol and 1-octene-3-ol) and alkenes(norbornene, cyclohexene, cyclooctene, styrene, -methylstyreneand trans-stilbene) were carried out in a round bottom flaskequipped with a magnetic stirrer and a water-cooled condenser. Typically, Fe3O4SiO2APTMSV-MIL-101 (containing %2.5 V)(40 mg) designated as catalyst 1 in acetonitril (5 mL), and substrate(20 mmol in 5 mL acetonitrile) were mixed. TBHP (24 mmol) wasthen added and the mixture was heated at reflux for several hours.After separation of the catalyst by means of an external magnet, thefiltrate plus authentic samples were subjected to GC and GC-Mass analyses
100%	With tributyl-n-octylphosphonium peroxotantalate; dihydrogen peroxide In water at 0℃; Schlenk technique; chemoselective reaction;

98%	With dihydrogen peroxide at 31.85℃; for 5h;
96%	With vanadium-pillared montmorillonite; dihydrogen peroxide In toluene; benzene for 5h; Ambient temperature; other unsaturated alcohols, var. reaction time;
96%	With vanadium-pillared montmorillonite (V-PILC); dihydrogen peroxide In benzene for 5h; Ambient temperature;
88%	With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate In dichloromethane; toluene at -20℃; for 4.66667h; Molecular sieve;
86%	With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium In dichloromethane
85%	With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium In hexane at 20℃; for 5h;
82%	With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium In 2,2,4-trimethylpentane; dichloromethane
81%	With dihydrogen peroxide; sodium acetate In methanol; water at 20℃; for 5h; pH=4.5;
79%	With Oxone; ethylenediaminetetraacetic acid; tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate; acetone In water; acetonitrile for 2h;
71%	With 1,1-Diphenylmethanol; oxygen In various solvent(s) at 50℃; for 24h;
68%	With tert.-butylhydroperoxide In hexane for 2h; microwave irradiation;
63%	With tert.-butylhydroperoxide In chloroform at 45℃; for 96h;
50%	With tert.-butylhydroperoxide; polymeric titanium(IV) 1,2-propanediolate In decane; hexane at 50℃; for 24h;
48%	With tert.-butylhydroperoxide; 4 A molecular sieve In toluene at 90℃; for 1h;
12%	With EtOCOC=(2-(5-Me-5-HOO-furyl))COCH₃ In dichloromethane at 0 - 5℃;
	Sharpless epoxidation;
67 % Chromat.	With oxygen; isobutyraldehyde In 1,2-dichloro-ethane at 25℃; for 4h;
	With N-hydroxyphthalimide; tetralin; oxygen In benzonitrile at 60℃; for 6h;
	With dihydrogen peroxide In 1,2-dichloro-ethane at 25℃; for 24h;
	With [ZnWZn₂(H₂O)2(ZnW₉O₃₄]^(12-)*tripodal org. polyammonium salt; dihydrogen peroxide In acetonitrile at 21℃; for 4h;
93 % Chromat.	With dihydrogen peroxide In acetonitrile at 20℃; for 2.5h;
	With ammonium acetate; dihydrogen peroxide In acetone at 10℃; for 4h;
	With Cumene hydroperoxide In Isopropylbenzene; chloroform for 6h; Inert atmosphere; Reflux;
	With 7H₂OLa⁽³⁺⁾2O₃₉PW₁₁^(7-)*11C₁₃H₃₀N⁽¹⁺⁾; dihydrogen peroxide In water; acetonitrile at 25℃; for 12h; chemoselective reaction;	2.5 Procedure for catalytic oxidation with H₂O₂ General procedure: In a typical experiment, 1 mmol substrate, 30% H2O2 aqueous solution, 0.25 mol% DA-La(PW11)2 and 0.2 ml acetonitrile (V(H2O2):V(CH3CN) = 1:2) were placed in a 20 ml glass bottle at room temperature and the reaction mixture was kept stirring vigorously. When the reaction completed, diethyl ether and water were added to the reaction mixture. The POM catalyst of DA-La(PW11)2 was precipitated in the organic layer and the corresponding product was extracted to the organic layer. After centrifuging the organic layer, the POM catalyst of DA-La(PW11)2 was recovered and the clear organic solution was analyzed by GC and identified by 1H NMR to determine the yield based on H2O2. Similar procedures were adopted for catalytic oxidation with H2O2 catalyzed by DDA-La(PW11)2, TDA-La(PW11)2, HDA-La(PW11)2 and ODA-La(PW11)2.
	With tert.-butylhydroperoxide; [MoBr(η³-C₃H₅)(CO)₂(8-aminoquinoline)] In decane; dichloromethane at 54.84℃; for 24h;	2.3. Catalytic tests General procedure: Complexes and materials were tested as catalysts in the epoxidation of cis-cycloctene, styrene, 1-octene, R-(+)limonene,geraniol, cis-3-hexene-1-ol and trans-2-hexene-1-ol, using tertbutylhydroperoxide (TBHP) as oxidant. The catalytic oxidation tests were carried out at 328 K under normal atmosphere in a reaction vessel equipped with a magnetic stirrer and a condenser. In a typical experiment, the vessel was loaded with olefin (100%), internal standard (DBE), catalyst (1%), oxidant (200%), and 3 mL of solvent. Addition of the oxidant determines the initial time of the reaction. The course of the reactions was monitored by quantitative GCanalysis by collecting samples at 10 min, 30 min, 1 h, 1 h 30 min, 2, 4, 6, 8, and 24 h of reaction. These samples were treated as described previously prior to injection in the GC column.
	With tert.-butylhydroperoxide In chloroform Reflux; Inert atmosphere;
	With tert.-butylhydroperoxide In decane; dichloromethane at 54.84℃;	4.3 Catalytic tests General procedure: The complexes and materials were tested in the catalytic epoxidation of cis-cyclooctene (cy8), 1-octene (1-oct), styrene (sty), geraniol (ger), cis-hex-3-en-1-ol (cis), trans-hex-2-en-1-ol (trans) and R(+)-limonene (R-lim), using tert-butylhydroperoxide (TBHP) as oxidant. The catalytic oxidation tests were carried out at 328 K under normal atmosphere in a reaction vessel equipped with a magnetic stirrer and a condenser. In a typical experiment the vessel was loaded with olefin or alcohol (100 mol%), internal standard (dibutyl ether), catalysts (1 mol%), oxidant (200 mol%), and 3mL of solvent. Addition of the oxidant determines the initial time of the reaction. The course of the reactions was monitored by quantitative GC-analysis by collecting samples at 10, 30 min, 1 h and 1.5 h, then at 2, 4, 6, 8, and 24 h of reaction. These samples were treated as described previously prior to injection in the GC column [43].
	With tert.-butylhydroperoxide In chloroform Inert atmosphere; Reflux;	2.2. Catalytic epoxidation of olefins in the presence ofMo-APTS-AC catalyst General procedure: Epoxidation of olefins was carried out in a 25 ml roundbottom flask equipped with a condenser and a magnetic stir-rer. Tert-butyl hydroperoxide (TBHP, 80% in di-tertiary butylperoxide) and cumene hydroperoxides (CHP, 80% in cumene)were used as oxidants. In a typical procedure, to a mix-ture of catalyst (100 mg) and olefin (8 mmol) in chloroform(10 ml) was added oxidant (14.4 mmol) under nitrogen atmo-sphere and the mixture was refluxed for a given time. Sampleswere withdrawn periodically and after cooling and dilutionwith solvent were analyzed using a gas chromatograph (HP,Agilent 6890N) equipped with a capillary column (HP-5) anda flame ionization detector (FID). The products were quanti-fied using isooctane (8.75 mmol) as internal standard. GC-MS(gas chromatography-mass spectrometry) of the products wererecorded using a Shimadzu-14A fitted with a capillary column(CBP5-M25).
	With tert.-butylhydroperoxide; di-tert-butyl peroxide In chloroform for 2h; Reflux;	2.2.3. Catalytic epoxidation of olefins using Mo-AMP-CuBTC catalyst General procedure: As a typical procedure, the epoxidation reaction was carried out as follows: to a mixture of catalyst (100 mg) and olefin(8 mmol) in solvent (10 ml) was added oxidant (14.4 mmol). Tertbutyl hydroperoxide (TBHP, 80% in di-tertiary butyl peroxide), cumene hydroperoxide (CHP, 80% in cumene) and hydrogen peroxide (H2O2, 30% in water) were used as oxidants. The mixture was refluxed for various times and the final products were quantified with isooctane (8.75 mmol) as internal standard.
	With tert.-butylhydroperoxide; α-molybdenum trioxide In toluene at 109.84℃; for 4h;	In a typical experiment the vessel was loaded withthe olefin or the alcohol (100%), internal standard (dibutylether,DBE), catalyst (1%), oxidant (200%) and 3 mL of solvent (acetoni-trile, toluene or decane). The final volume of the reaction is ca. 6 mL.The addition of the oxidant determines the beginning of the reac-tion. Conversion, product yields and selectivity were monitoredby sampling periodically and analyzing them using a ShimadzuQP2100-Plus GC/MS system and a capillary column (TeknokromaTRB-5MS/TRB-1MS) operating in the linear velocity mode.
	With tert.-butylhydroperoxide In dichloromethane at 54.84℃; for 24h;	6 3.11. Catalytic studies General procedure: The materials were tested as catalysts in the epoxidationof olefins and allylic alcohols, such as cis-cyclooctene, styrene,1-octene, trans-hex-2-en-1-ol, cis-3-hex-1-ol, geraniol, and R-(+)-limonene, using t-butylhydroperoxide (tbhp) as oxidant (Aldrich,5.5 M in decane). The catalytic oxidation tests were carried out at328 K under air in a vessel equipped with a magnetic stirrer anda condenser. In a typical experiment, the vessel was loaded witholefin or alcohol (100%), internal standard (dibutyl ether, DBE),catalyst (175 mg), oxidant (200%), and 3 mL of dichloromethaneas solvent. The final volume of the reaction was ca. 6 mL. Addi-tion of the oxidant determined the initial time of the reaction.Conversion, product yields and stereochemistry were monitoredby sampling periodically and analyzing them using a ShimadzuQP2100-Plus GC/MS system and a capillary column (TeknokromaTRB-5MS/TRB-1MS or Restek Rt-DEXsm) operating in the lin-ear velocity mode. Leaching and recycling experiments, in general,were carried out as described above for trans-hex-2-en-1-ol epox-idation using material Si16-pyca-2 and Si16-pyca-1 as catalyst;conversion and product yields were monitored as described above.For the leaching experiments after 2 h reaction, the catalyst wasfiltered off, and the reactions continued under the same conditions.In the case of the recycling experiments, after each cycle (24 h),the catalyst was filtered, washed with dichloromethane, and driedprior to reuse in a new catalytic cycle.
	With WO<SUB>2</SUB>(acac)<SUB>2</SUB>; dihydrogen peroxide In dichloromethane at 20℃; for 2.5h;
	With tert.-butylhydroperoxide In chloroform for 8h; Inert atmosphere; Reflux;	Catalytic epoxidation of olefins and allylic alcoholsin the presence of Mo-dtc-SCMNPs General procedure: The catalytic tests for the epoxidation reactions were performedin the presence of Mo-dtc-SCMNPs as catalyst andtert-butyl hydroperoxide (TBHP, 80% in di-tert-butylperoxide) as oxidant. The general procedure was as follows:to a mixture of 50 mg catalyst and 4 mmol olefin orallyl alcohol in 5 cm3 chloroform was added 0.75 cm3TBHP and the mixture was refluxed under nitrogen atmospherefor appropriate time. Samples were withdrawn ingiven times and were analyzed using GC analysis.
	With 8Na⁽¹⁺⁾3Ni⁽²⁺⁾2C₂H₈N₂28H₂ONb₁₀O₃₂^(14-); dihydrogen peroxide In water at 35℃; for 1h;
	With 0.042C₁₄H₂₈N₂O₃Si^(2-)0.036F₆P^(1-)0.0225La⁽³⁺⁾0.72H₂OPW₁₁O₃₉*(Mg_0.75Al_0.25(OH)1.87); dihydrogen peroxide In acetonitrile at 70℃; for 2h;
	With tert.-butylhydroperoxide In chloroform Reflux; Inert atmosphere;
	With tert.-butylhydroperoxide; dioxo(bis(2-pyridylcarbonyl)amido)vanadium(V) In water; acetonitrile at 80℃; for 4h;
	With tert.-butylhydroperoxide In acetonitrile for 3h; Reflux;
	With tert.-butylhydroperoxide In decane; toluene at 79.84℃; for 80h;	2.3. Catalytic epoxidation of olefins General procedure: Catalytic tests were carried out in a Carousel 12 Plus ReactionStation from Radleys. A given amount (1.6 mmol) of the olefin substrates- cis-cyclooctene, styrene, 1-octene, trans-2-hexen-1-ol, R-(+)-limonene - was mixed with dibutylether (1.6 mmol) (internalstandard) and 15 μL (5 mol %) of tert-butyl hydroperoxide (5.5M solutionin decane; tbhp). Then the catalyst was added to this mixture.This was either 10 mL of exfoliated materials ExHTCo/Al-met-Au(0.016 mol Au) with an extra 5 mL of acetonitrile or 100 mg of HTCo/Almet-Au (0.016 mol Au) bulk catalyst with 8 mL of toluene. The magneticallystirred mixture was heated to 353 K and kept for 80 h.
	With tert.-butylhydroperoxide In acetonitrile at 80℃; for 9h;	2.2. Catalytic procedure General procedure: In a typical procedure, substrate (10 mmol) and TBHP (12 mmol)were added to the desired amount of catalyst in acetonitrile (5 mL)and the mixture heated at reflux for the appropriate time. Uponcompletion, the catalyst was collected by filtration on a fine frit,washed with acetonitrile and then dried in an oven. The catalystwas reused at least three times without a significant decrease incatalytic activity or selectivity. The products were identified withGC and GC-Mass techniques.
	With 4Co⁽²⁺⁾22H₂O10K⁽¹⁺⁾*O₆₈P₂W₁₈^(18-); dihydrogen peroxide; Aliquat 336 In water; 1,2-dichloro-ethane at 15℃; for 3h;	2.2.2 Catalysis reactions and analysis of the products of reaction General procedure: All catalysis reactions were performed in a biphasic 1,2-dichloroethane/aqueous H2O2 mixture using a 10mL glass vial that was fitted with a plastic screw top and teflon-coated magnetic stir bar, which was stirred using a Corning immersible stir pad (Model No. 440837). The screw top had a pinhole to vent any oxygen buildup from dismutation of H2O2. Typically, a sample of catalyst (1.0mL, 5μmol, 20 equivalents of Aliquat 336) was transferred to a 5mL volumetric flask, followed by 5.0mmol of organic substrate (0.35-1.15mL) and 2.5mmol (0.39mL) of t-butylbenzene (as an internal GC standard) and the solution made up to 5.00mL with 1,2-dichloroethane. This procedure gave a constant concentration of 1mM of catalyst for each reaction, with a constant substrate concentration of 1.000M. The resulting solution was then transferred to the glass vial, and a 2-fold excess of aqueous H2O2 (~30% v/v, ~10mmol, 1mL, pH ~3.2) over organic substrate was added. This always resulted in a biphasic mixture. The mixture was stirred vigorously at the designated temperature for 3h, after which time the phases were allowed to separate by standing (5min). The organic phase, both prior to the addition of the aqueous H2O2 and following reaction after standing, was analyzed by direct injection into a gas chromatograph. For the lower molecular weight allylic alcohols allyl alcohol, 2-methyl-2-propen-1-ol and trans-crotyl alcohol, but less so for 3-methyl-2-buten-1-ol, some transfer of the alcohol to the aqueous phase took place during the reaction, which resulted in greater apparent reactivity. This was significantly reduced by adding KCl (0.30g) and stirring for 1-2min, before the phase separation stage and subsequent GC analysis. Gas-phase chromatographic analyses were performed on a Shimadzu 17A gas chromatograph with a 15m AT-Aquawax capillary column, coupled to a Shimadzu C-R8A Chromatopac integrator as described previously [14].
	With tert.-butylhydroperoxide In acetonitrile Reflux;
	With tert.-butylhydroperoxide In acetonitrile for 10h; Reflux;	2.6. [VO(His) 2 ]complexUiO-66-NH 2 as epoxidation catalyst General procedure: To study the catalytic activity of [VO(His) 2 ]complexUiO-66- NH 2 , epoxidation reaction of some allyl alcohols in acetonitrile were carried out by heating the desired amount of catalyst, sub- strate (10 mmol) and TBHP (12 mmol) in acetonitrile (5 mL) at re- flux for the desired time. Upon completion, the catalyst was separated by centrifugation, washed with ethanol and acetonitrile sol- vents and finally dried in an oven at 100 °C. The filtrate was then injected to GC and GC-Mass analysis for identification of products.

Reference： [1]Hamidipour, Lida; Farzaneh, Faezeh [Comptes Rendus Chimie, 2014, vol. 17, # 9, p. 927 - 933]
[2]Farzaneh, Faezeh; Sadeghi, Yasaman [Journal of Molecular Catalysis A: Chemical, 2015, vol. 398, p. 275 - 281]
[3]Ma, Wenbao; Chen, Chen; Kong, Kang; Dong, Qifeng; Li, Kun; Yuan, Mingming; Li, Difan; Hou, Zhenshan [Chemistry - A European Journal, 2017, vol. 23, # 30, p. 7287 - 7296]
[4]Kamata, Keigo; Yamaguchi, Kazuya; Mizuno, Noritaka [Chemistry - A European Journal, 2004, vol. 10, # 19, p. 4728 - 4734]
[5]Choudary, B. M.; Valli, V. L. K.; Prasad, A. Durga [Journal of the Chemical Society. Chemical communications, 1990, # 9, p. 721 - 722]
[6]Choudary, B. M.; Valli, V. L. K.; Prasad, A. Durga [Journal of the Chemical Society. Chemical communications, 1990, # 9, p. 721 - 722]
[7]Blasco, Pilar; Chen, Delin; Chen, Sheng; Li, Xuechen; Po, Kathy Hiu Laam [Organic Letters, 2020]
[8]Rayner, Christopher M.; Westwell, Andrew D. [Tetrahedron Letters, 1992, vol. 33, # 17, p. 2409 - 2412]
[9]Lattanzi, Alessandra; Leadbeater, Nicholas E. [Organic Letters, 2002, vol. 4, # 9, p. 1519 - 1521]
[10]Dittmer, Donald C.; Zhang, Yanzhi; Discordia, Robert P. [Journal of Organic Chemistry, 1994, vol. 59, # 5, p. 1004 - 1010]
[11]Prat, Denis; Lett, Robert [Tetrahedron Letters, 1986, vol. 27, # 6, p. 707 - 710]
[12]Frohn, Michael; Wang, Zhi-Xian; Shi, Yian [Journal of Organic Chemistry, 1998, vol. 63, # 18, p. 6425 - 6426]
[13]Iwahama, Takahiro; Sakaguchi, Satoshi; Ishii, Yasutaka [Heterocycles, 2000, vol. 52, # 2, p. 693 - 705]
[14]Della Sala, Giorgio; Giordano, Lucia; Lattanzi, Alessandra; Proto, Antonio; Scettri, Arrigo [Tetrahedron, 2000, vol. 56, # 22, p. 3567 - 3573]
[15]Antonioletti, R.; Bonadies, F.; Locati, L.; Scettri, A. [Tetrahedron Letters, 1992, vol. 33, # 22, p. 3205 - 3206]
[16]Massa; Scettri [Synlett, 2000, # 9, p. 1348 - 1350]
[17]Dusi, Marco; Mueller, Christian A.; Mallat, Tamas; Baiker, Alfons [Chemical Communications, 1999, # 2, p. 197 - 198]
[18]Antonioletti, R.; Bonadies, F.; Pesci, S.; Scettri, A. [Tetrahedron Letters, 1992, vol. 33, # 27, p. 3947 - 3948]
[19]Legters, J.; Thijs, L.; Zwanenburg, B. [Tetrahedron Letters, 1989, vol. 30, # 36, p. 4881 - 4884]
[20]Hamamoto, Masatoshi; Nakayama, Kouichi; Nishiyama, Yutaka; Ishii, Yasutaka [Journal of Organic Chemistry, 1993, vol. 58, # 23, p. 6421 - 6425]
[21]Iwahama, Takahiro; Hatta, Gou; Sakaguchi, Satoshi; Ishii, Yasutaka [Chemical Communications, 2000, # 2, p. 163 - 164]
[22]Ben-Daniel, Revital; Khenkin, Alexander M.; Neumann, Ronny [Chemistry - A European Journal, 2000, vol. 6, # 20, p. 3722 - 3728]
[23]Vasylyev, Maxym V.; Neumann, Ronny [Journal of the American Chemical Society, 2004, vol. 126, # 3, p. 884 - 890]
[24]Dinda, Subhajit; Roy Chowdhury, Sujoy; Abdul Malik; Bhattacharyya, Ramgopal [Tetrahedron Letters, 2005, vol. 46, # 2, p. 339 - 341]
[25]Zhong, Sheng; Tan, Yueming; Fu, Zaihui; Xie, Qingji; Xie, Fang; Zhou, Xiaoping; Ye, Zhengpei; Peng, Guosheng; Yin, Dulin [Journal of Catalysis, 2008, vol. 256, # 1, p. 154 - 158]
[26]Location in patent: experimental part Masteri-Farahani; Tayyebi [Journal of Molecular Catalysis A: Chemical, 2011, vol. 348, # 1-2, p. 83 - 87]
[27]Zhao, Shen; Jia, Yueqing; Song, Yu-Fei [Applied Catalysis A: General, 2013, vol. 453, p. 188 - 194]
[28]Saraiva, Marta S.; Nunes, Carla D.; Nunes, Teresa G.; Calhorda, Maria José [Applied Catalysis A: General, 2013, vol. 455, p. 172 - 182]
[29]Mohammadikish; Masteri-Farahani; Mahdavi [Journal of Magnetism and Magnetic Materials, 2014, vol. 354, p. 317 - 323]
[30]Saraiva, Marta S.; Fernandes, Cristina I.; Nunes, Teresa G.; Nunes, Carla D.; Calhorda, Maria José [Journal of Organometallic Chemistry, 2014, vol. 751, p. 443 - 452]
[31]Masteri-Farahani; Abednatanzi [Applied Catalysis A: General, 2014, vol. 478, p. 211 - 218]
[32]Abednatanzi, Sara; Abbasi, Alireza; Masteri-Farahani, Majid [Journal of Molecular Catalysis A: Chemical, 2015, vol. 399, p. 10 - 17]
[33]Fernandes, Cristina I.; Capelli, Silvia C.; Vaz, Pedro D.; Nunes, Carla D. [Applied Catalysis A: General, 2015, vol. 504, p. 344 - 350]
[34]Saraiva, Marta S.; Fernandes, Cristina I.; Nunes, Teresa G.; Calhorda, Maria José; Nunes, Carla D. [Applied Catalysis A: General, 2015, vol. 504, p. 328 - 337]
[35]Li, Tengfei; Wang, Zelin; Chen, Wei; Miras, Haralampos N.; Song, Yu-Fei [Chemistry - A European Journal, 2017, vol. 23, # 5, p. 1069 - 1077]
[36]Masteri-Farahani, Majid; Modarres, Maryam [Monatshefte fur Chemie, 2017, vol. 148, # 8, p. 1403 - 1410]
[37]Li, Li; Niu, Yanjun; Dong, Kaili; Ma, Pengtao; Zhang, Chao; Niu, Jingyang; Wang, Jingping [RSC Advances, 2017, vol. 7, # 46, p. 28696 - 28701]
[38]Li, Tengfei; Zhang, Wei; Chen, Wei; Miras, Haralampos N.; Song, Yu-Fei [ChemCatChem, 2018, vol. 10, # 1, p. 188 - 197]
[39]Masteri-Farahani, Majid; Shahsavarifar, Samaneh [Applied Organometallic Chemistry, 2018, vol. 32, # 2]
[40]Azarkamanzad, Zahra; Farzaneh, Faezeh; Maghami, Mahboobeh; Simpson, Jim; Azarkish, Mohammad [Applied Organometallic Chemistry, 2018, vol. 32, # 3]
[41]Farzaneh, Faezeh; Asgharpour, Zeinab [Applied Organometallic Chemistry, 2019, vol. 33, # 5]
[42]Leandro, Sónia R.; Fernandes, Cristina I.; Viana; Mourato; Vaz, Pedro D.; Nunes, Carla D. [Applied Catalysis A: General, 2019, vol. 584]
[43]Geravand, Elham; Farzaneh, Faezeh; Ghiasi, Mina [Journal of Molecular Structure, 2019, vol. 1198]
[44]Abram, Paulus Hengky; Burns, Robert C.; Li, Lichun [Inorganica Chimica Acta, 2020, vol. 499]
[45]Farzaneh, Faezeh; Ahmadi, Zahra; Azarkamanzad, Zahra; Ghahremani, Maryam [Applied Organometallic Chemistry, 2021, vol. 35, # 4]
[46]Farzaneh, Faezeh; Geravand, Elham; Ghiasi, Mina [Journal of Molecular Structure, 2022, vol. 1253]

13
[ 928-95-0 ]
[ 89395-00-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	With dihydrogen peroxide In water at 31.84℃; for 5h;
94%	With dihydrogen peroxide In acetonitrile at 50℃; for 4h;
90%	With dihydrogen peroxide; tetraphenylphosphonium; sodium hydrogencarbonate In acetonitrile at 25℃; for 0.5h;

89%	With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 16h;
87%	With tert.-butylhydroperoxide; 4 A molecular sieve In decane; dichloromethane at 20℃; for 6h;
80%	With pyridine-3-carbonitrile; dihydrogen peroxide; methyltrioxorhenium(VII) In dichloromethane at 24℃; for 6h;
78%	With C₉H₆NO^(1-)C₂₄H₂₀P⁽¹⁺⁾MoO⁽⁴⁺⁾*2O₂^(2-); dihydrogen peroxide; sodium hydrogencarbonate In acetonitrile at 25℃; for 0.33h;
78%	With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 24h; optical yield given as %de; stereoselective reaction;
68%	With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 2h;
67%	With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 25℃; for 15h;
64%	With ethylenediaminetetraacetic acid; 1,1,1-trifluoro-2-propanone; dihydrogen peroxide; potassium carbonate In acetonitrile at 0℃; for 10h;
64%	With dihydrogen peroxide; potassium carbonate; acetonitrile In water at 0℃; for 4h;
63%	With tert.-butylhydroperoxide; 4 A molecular sieve In chloroform at 45℃; for 96h;
24%	With Oxone; Cyclohexylidenepyrrolidinium tetrafluoroborate; sodium hydrogencarbonate In acetonitrile at 25℃; for 16h;
	With 3-chloro-benzenecarboperoxoic acid
	With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃;
67 % Chromat.	With oxygen; isobutyraldehyde In 1,2-dichloro-ethane for 14h; Ambient temperature;
	With tert.-butylhydroperoxide In carbon dioxide at 25℃; for 24h; Yield given;
	With tert.-butylhydroperoxide In carbon dioxide; water at 45℃; for 24h; Yield given;
	With 3-chloro-benzenecarboperoxoic acid In chloroform at 20℃; for 1h;
	With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 25℃; for 15h;
32.50 % Chromat.	With tert.-butylhydroperoxide In dichloromethane; toluene at 64.85℃; for 5h;
	With 3-chloro-benzenecarboperoxoic acid
89 % Chromat.	With dihydrogen peroxide In acetonitrile at 50℃; for 6h;
	With dihydrogen peroxide In water at 50℃; for 2.5h;
89 %Spectr.	With (TBA)2[SeO₄{WO(O₂)2}2]; dihydrogen peroxide In [D₃]acetonitrile; water at 31.84℃; for 3h;
> 95 % de	With tert.-butylhydroperoxide In decane; toluene at 109.84℃;
80 %Chromat.	With dihydrogen peroxide In water at 34.84℃; for 7h; Green chemistry;
	With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃;

Reference： [1]Kamata, Keigo; Yamaguchi, Kazuya; Hikichi, Shiro; Mizuno, Noritaka [Advanced Synthesis and Catalysis, 2003, vol. 345, # 11, p. 1193 - 1196]
[2]Doherty, Simon; Knight, Julian G.; Ellison, Jack R.; Weekes, David; Harrington, Ross W.; Hardacre, Christopher; Manyar, Haresh [Green Chemistry, 2012, vol. 14, # 4, p. 925 - 929]
[3]Maiti, Swarup K.; Dinda, Subhajit; Gharah, Narottam; Bhattacharyya, Ramgopal [New Journal of Chemistry, 2006, vol. 30, # 3, p. 479 - 489]
[4]Chini, Marco; Crotti, Paolo; Flippin, Lee A.; Gardelli, Christina; Giovani, Elena; et al. [Journal of Organic Chemistry, 1993, vol. 58, # 5, p. 1221 - 1227]
[5]Massa, Antonio; D'Ambrosi, Antonietta; Proto, Antonio; Scettri, Arrigo [Tetrahedron Letters, 2001, vol. 42, # 10, p. 1995 - 1998]
[6]Adolfsson; Coperet; Chiang; Yudin [Journal of Organic Chemistry, 2000, vol. 65, # 25, p. 8651 - 8658]
[7]Maiti, Swarup K.; Dinda, Subhajit; Bhattacharyya, Ramgopal [Tetrahedron Letters, 2008, vol. 49, # 43, p. 6205 - 6208]
[8]Location in patent: experimental part Cresswell, Alexander J.; Davies, Stephen G.; Lee, James A.; Morris, Melloney J.; Roberts, Paul M.; Thomson, James E. [Journal of Organic Chemistry, 2011, vol. 76, # 11, p. 4617 - 4627]
[9]Tanveer, Kashif; Jarrah, Kareem; Taylor, Mark S. [Organic Letters, 2015, vol. 17, # 14, p. 3482 - 3485]
[10]Mordini, Alessandro; Pecchi, Sabina; Capozzi, Giuseppe; Capperucci, Antonella; Degl'Innocenti, Alessandro; et al. [Journal of Organic Chemistry, 1994, vol. 59, # 17, p. 4784 - 4790]
[11]Shu; Shi [Journal of Organic Chemistry, 2000, vol. 65, # 25, p. 8807 - 8810]
[12]Current Patent Assignee: COLORADO STATE UNIVERSITY SYSTEM - US6369245, 2002, B1 Location in patent: Example 8
[13]Palombi, Laura; Bonadies, Francesco; Scettri, Arrigo [Tetrahedron, 1997, vol. 53, # 33, p. 11369 - 11376]
[14]Minakata; Takemiya; Nakamura; Ryu; Komatsu [Synlett, 2000, # 12, p. 1810 - 1812]
[15]Gorthey, Lee Ann; Vairamani, Mariappanadar; Djerassi, Carl [Journal of Organic Chemistry, 1984, vol. 49, # 9, p. 1511 - 1517]
[16]Mulzer, Johann; Lammer, Ortrud [Chemische Berichte, 1986, vol. 119, # 7, p. 2178 - 2190]
[17]Takai, Toshihiro; Hata, Eiichiro; Yamada, Tohru; Mukaiyama, Teruaki [Bulletin of the Chemical Society of Japan, 1991, vol. 64, # 8, p. 2513 - 2518]
[18]Pesiri, David R.; Morita, David K.; Glaze, William; Tumas, William [Chemical Communications, 1998, # 9, p. 1015 - 1016]
[19]Haas, Geoffrey R.; Kolis, Joseph W. [Tetrahedron Letters, 1998, vol. 39, # 33, p. 5923 - 5926]
[20]Miyaoka, Hiroaki; Shigemoto, Tatsuya; Shinohara, Ikuo; Suzuki, Atsushi; Yamada, Yasuji [Tetrahedron, 2000, vol. 56, # 41, p. 8077 - 8081]
[21]Thurner, Angelika; Faigl, Ferenc; Toke, László; Mordini, Alessandro; Valacchi, Michela; Reginato, Gianna; Czira, Gábor [Tetrahedron, 2001, vol. 57, # 38, p. 8173 - 8180]
[22]Khedher; Ghorbela; Tuel [Journal of Chemical Research - Part S, 2003, # 7, p. 390 - 394]
[23]Hirai, Atsushi; Yu, Xiao-Qiang; Tonooka, Terumichi; Miyashita, Masaaki [Chemical Communications, 2003, # 19, p. 2482 - 2483]
[24]Liu, Peng; Wang, Hong; Feng, Zhaochi; Ying, Pinliang; Li, Can [Journal of Catalysis, 2008, vol. 256, # 2, p. 345 - 348]
[25]Location in patent: scheme or table Liu, Peng; Wang, Changhao; Li, Can [Journal of Catalysis, 2009, vol. 262, # 1, p. 159 - 168]
[26]Location in patent: scheme or table Kamata, Keigo; Hirano, Tomohisa; Kuzuya, Shinjiro; Mizuno, Noritaka [Journal of the American Chemical Society, 2009, vol. 131, p. 6997 - 7004]
[27]Fernandes, Cristina I.; Stenning, Gavin B. G.; Taylor, James D.; Nunes, Carla D.; D. Vaz, Pedro [Advanced Synthesis and Catalysis, 2015, vol. 357, # 14-15, p. 3127 - 3140]
[28]Zhao, Wei; Yang, Chunxia; Cheng, Zhiguo; Zhang, Zhenghui [Green Chemistry, 2016, vol. 18, # 4, p. 995 - 998]
[29]Hill, J. Gordon; Sharpless, K. Barry; Exon, Christopher M.; Regenye, Ronald [Organic Syntheses, 1985, vol. 63, p. 66 - 66]

14
[ 928-95-0 ]
[ 89321-71-1 ]

Yield	Reaction Conditions	Operation in experiment
90%	With C₉₆H₁₄₂N₂O₄; WO<SUB>2</SUB>(acac)<SUB>2</SUB>; dihydrogen peroxide; sodium chloride In dichloromethane; water at 20℃; for 3h; Green chemistry; enantioselective reaction;
86%	With C₃₀H₂₄N₂O₇W; dihydrogen peroxide; sodium hydrogencarbonate In water; acetonitrile at 25℃; for 0.75h;
86%	With titanium(IV) isopropylate; diethyl (2R,3R)-tartrate; Cumene hydroperoxide In dichloromethane at -22℃; Molecular sieve;

83%	With titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate In dichloromethane at -20℃; for 14h;
82%	With titanium(IV) isopropylate; tert.-butylhydroperoxide; 4 A molecular sieve In dichloromethane at -20℃; for 3h;
81%	With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate
80%	With tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate In dichloromethane at -20℃; for 48h; Molecular sieve;	14.c Example 14 14-c The procedure indicated in the preceding example (14-b) was repeated but by carrying out the reaction with Ti(OiPr)4(253 μmol) instead of Ta(OEt)5. After reaction, analysis of the solution by GC gives a propyloxiranemethanol yield of 80%, a conversion of the trans-2-hexen-1-ol of 99%, i.e. a selectivity of 81%, and an enantiomeric excess of 96% (predominantly (S,S)-propyloxiranemethanol).
78%	With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate In dichloromethane; toluene at -70 - 0℃; for 2h; Inert atmosphere; enantioselective reaction;
69%	With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate In dichloromethane
69%	With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate In dichloromethane
68%
66%	With titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diethyl tartrate In dichloromethane; toluene at -20℃; Inert atmosphere; Molecular sieve; optical yield given as %ee;
65%	With titanium(IV) isopropylate; tert.-butylhydroperoxide; (-)-diethyl tartrate
57%	Stage #1: (E)-2-Hexen-1-ol With C₇₆H₅₆N₂O₂; niobium(V) isopropoxide In chloroform; sodium chloride at 40℃; for 0.5h; Stage #2: With dihydrogen peroxide In chloroform; water; sodium chloride at 40℃; Stage #3: With sodium tetrahydroborate optical yield given as %ee; enantioselective reaction;
52%	With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate In dichloromethane at -30℃; for 72h;
40%	With tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate In dichloromethane at -20℃; for 48h;	14.a Example 14 14-a An amount of 250 mg of the solid prepared in Example 4-b, exhibiting a content by mass of tantalum of 5.40% (75 μmol of Ta), is placed in a 50 ml round-bottomed flask with approximately 150 mg of thoroughly dehydrated powdered zeolite 3 , and 18 ml of dichloromethane are added. The combined mixture is cooled to -20° C. and 84 μl of 1.0M solution of diethyl (+)-(R,R)-tartrate (84 μmol) are introduced. The suspension is left to stir at this temperature for 15 hours, then 188 mg of trans-2-hexen-1-ol (1.9 mmol) are introduced and the mixture is left to stir for 30 min before introducing 0.6 ml of a 6.5M solution of TBHP (tBuOOH) in dichloromethane (approximately 3.9 mmol). The medium is left for 48 hours at -20° C. in order for the epoxidation reaction to take place. It is subsequently filtered through a sintered glass under argon and the solid catalyst is washed four times with dichloromethane at ambient temperature and the solutions are combined together. Analysis by GC gives a propyloxiranemethanol yield of 40%, a conversion of the trans-2-hexen-1-ol of 48%, i.e. a selectivity of 83%, and an enantiomeric excess of 90% (predominantly (S,S)-propyloxiranemethanol).
31%	With tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate In dichloromethane at -20℃; for 48h;	12; 13 Example 12 Example 12 This example and those which follow show that the catalysts described in the preceding examples apply not only to allyl alcohol itself but also to numerous other alcohols. An amount of 500 mg of the solid prepared in Example 4-b, exhibiting a content by mass of tantalum of 5.40% (149 μmol of Ta) is placed in a 100 ml round-bottomed flask with 40 ml of solvent (CH2Cl2). The combined mixture is cooled to -20° C., 31 mg of diethyl (+)-tartrate (160 μmol) are introduced and the mixture is left to stir at -20° C. for 15 hours. 400 mg of trans-2-hexen-1-ol (4.0 mmol) are then added and, 30 minutes later, 1.6 ml of a 6.0M solution of TBHP in dichloromethane (9.6 mmol). The medium is left at -20° C. for 48 hours in order for the epoxidation reaction to take place. The medium is filtered through a sintered glass under argon, the solid catalyst is washed four times with dichloromethane at ambient temperature and the solutions are combined together. Analysis by GC gives a propyloxiranemethanol yield of 34%, a conversion of the trans-2-hexen-1-ol of 35%, i.e. a selectivity of 97%, and an enantiomeric excess of 89% (predominantly (S,S)-propyloxiranemethanol). Example 13; [00163] This example illustrates the fact that the catalyst described in Example 12 can be recycled without a significant loss in activity. [00164] The solid catalyst of Example 12, after having been washed four times with dichloromethane on a sintered glass at the end of the reaction (1st use), as was mentioned, is reused for a fresh reaction, the conditions of Example 12 being exactly reproduced. The results are then very similar to those obtained during the first use, with a propyloxiranemethanol yield of 31%, a conversion of the trans-2-hexen-1-ol of 35%, i.e. a selectivity of 89%, and an enantiomeric excess of 93% (predominantly (S,S)-propyloxiranemethanol).
31%	With tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate In dichloromethane at -20℃; for 48h;	15 Example 15; [00169] A mass of 230 mg of the solid prepared as indicated in Example 2-a, exhibiting a content by mass of tantalum of 4.87% (62 μmol of Ta), is placed in a 50 ml round-bottomed flask under an argon atmosphere and 15 ml of dichloromethane are added. The suspension is cooled to -20° C. and 70 μl of a 1.0M solution of diethyl (+)-tartrate (70 μmol) are added thereto. The medium is left to stir under an argon atmosphere for 48 hours at -20° C. An amount of 155 mg of propyloxiranemethanol (1.55 mmol) is subsequently introduced and the combined mixture left to stir for 30 minutes. An amount of 0.6 ml of a 6.0M solution of TBHP in dichloromethane (3.6 mmol) is added and the solution is left to stir under argon for 48 hours at -20° C. A propyloxiranemethanol yield of 31% and a degree of conversion of the trans-2-hexen-1-ol of 33%, thus a selectivity of 94%, for an enantiomeric excess of 90% (predominantly (S,S)-propyloxiranemethanol) are obtained. [00170] After recycling the catalyst as in Example 13 and by carrying out the reaction under the same conditions as during the first use, a propyl-oxiranemethanol yield of 23% and a degree of conversion of the trans-2-hexen-1-ol of 26%, thus a selectivity of 88%, for an enantiomeric excess of 90% (predominantly (S,S)-propyloxiranemethanol) are obtained.
25%	With tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate In dichloromethane at -20℃; for 48h;	16 Example 16 Example 16 An amount of 675 mg of the solid prepared as indicated in Example 4-a, exhibiting a content by mass of tantalum of 0.67% (25 μmol of Ta), is placed in a 50 ml round-bottomed flask under an argon atmosphere and 12 ml of dichloromethane are added. The combined mixture is cooled to -20° C. and 28 μl of 1.0M solution of diethyl (+)-(R,R)-tartrate (28 μmol) are introduced. The suspension is left to stir at this temperature for 15 hours, then 125 mg of trans-2-hexen-1-ol (1.25 mmol) are introduced and the mixture is left for 30 min before introducing 0.4 ml of a 6.5M solution of TBHP (tBuOOH) in dichloromethane (approximately 2.6 mmol). The medium is left for 48 hours at -20° C. in order for the epoxidation reaction to take place. The medium is filtered through a sintered glass under argon and the solid catalyst is washed four times with dichloromethane at ambient temperature and the solutions are combined together. Analysis by GC gives a propyloxiranemethanol yield of 25%, a conversion of the trans-2-hexen-1-ol of 33%, i.e. a selectivity of 75%, and an enantiomeric excess of 90% (predominantly (S,S)-propyloxiranemethanol).
	With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; 3 A molecular sieve In 2,2,4-trimethylpentane; dichloromethane at -20℃; for 3h;
	With titanium(IV) isopropylate; tert.-butylhydroperoxide; molecular sieve; diethyl (2R,3R)-tartrate In 2,2,4-trimethylpentane; dichloromethane at -20℃; for 48h;
	With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; 3 A molecular sieve 1.) CH₂Cl₂, -20 deg C, 15 min, 2.) isooctane, 4 h; Yield given. Multistep reaction;
	With titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate In dichloromethane at -20℃;
	With titanium(IV) isopropylate; tert.-butylhydroperoxide; chiral DET
1.06 g	With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate In dichloromethane at -30℃; for 72h;
	With titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate at -20℃;

Reference： [1]Wang, Chuan; Yamamoto, Hisashi [Journal of the American Chemical Society, 2014, vol. 136, # 4, p. 1222 - 1225]
[2]Location in patent: experimental part Maiti, Swarup K.; Dinda, Subhajit; Banerjee, Surajit; Mukherjee, Alok K.; Bhattacharyya, Ramgopal [European Journal of Inorganic Chemistry, 2008, # 12, p. 2038 - 2051]
[3]Location in patent: scheme or table Srinivas; Sai Pavan Kumar; China Raju; Jayathirtha Rao; Naidu; Ramakrishna; Diwan, Prakash V. [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 20, p. 5915 - 5918]
[4]Venkateswara Rao; Kumar, V. Satish; Nagarajan; Sitaramaiah; Rama Rao [Tetrahedron Letters, 1996, vol. 37, # 47, p. 8613 - 8616]
[5]Perez, Alice L.; Gries, Gerhard; Gries, Regine; Giblin-Davis, Robin M.; Oehlschlager, A. Cameron [Journal of Chemical Ecology, 1994, vol. 20, # 10, p. 2653 - 2672]
[6]Ito, Hisanaka; Sato, Azusa; Taguchi, Takeo [Tetrahedron Letters, 1997, vol. 38, # 27, p. 4815 - 4818]
[7]Current Patent Assignee: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE - US6642170, 2003, B1 Location in patent: Page/Page column 19
[8]Hill, J. Gordon; Sharpless, K. Barry; Exon, Christopher M.; Regenye, Ronald [Organic Syntheses, 1985, vol. 63, p. 66 - 66]
[9]Rayner, Christopher M.; Westwell, Andrew D. [Tetrahedron Letters, 1992, vol. 33, # 17, p. 2409 - 2412]
[10]Rayner; Sin; Westwell [Tetrahedron Letters, 1992, vol. 33, # 47, p. 7237 - 7240]
[11]Nair; Jahnke [Tetrahedron, 1987, vol. 43, # 19, p. 4257 - 4264]
[12]Li, Xiaoyong; Borhan, Babak [Journal of the American Chemical Society, 2008, vol. 130, # 48, p. 16126 - 16127]
[13]Thijs, Lambertus; Waanders, Peter P.; Stokkingreef, Edwin H. M.; Zwanenburg, Binne [Recueil des Travaux Chimiques des Pays-Bas, 1986, vol. 105, p. 332 - 337]
[14]Location in patent: scheme or table Egami, Hiromichi; Oguma, Takuya; Katsuki, Tsutomu [Journal of the American Chemical Society, 2010, vol. 132, # 16, p. 5886 - 5895]
[15]Pickenhagen, Wilhelm; Broenner-Schindler, Helene [Helvetica Chimica Acta, 1984, vol. 67, p. 947 - 952]
[16]Current Patent Assignee: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE - US6642170, 2003, B1 Location in patent: Page/Page column 19
[17]Current Patent Assignee: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE - US6642170, 2003, B1 Location in patent: Page/Page column 18
[18]Current Patent Assignee: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE - US6642170, 2003, B1 Location in patent: Page/Page column 19-20
[19]Current Patent Assignee: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE - US6642170, 2003, B1 Location in patent: Page/Page column 20
[20]Martin, Victor S.; Ode, Jesus M.; Palazon, Jose M.; Soler, Marcos A. [Tetrahedron Asymmetry, 1992, vol. 3, # 4, p. 573 - 580]
[21]Ghosh, Arun K.; Lee, Hee Yoon; Thompson, Wayne J.; Culberson, Chris; Holloway, M. Katharine; et al. [Journal of Medicinal Chemistry, 1994, vol. 37, # 8, p. 1177 - 1188]
[22]Rodriguez, Carmen M.; Martin, Tomas; Ramirez, Miguel A.; Martin, Victor S. [Journal of Organic Chemistry, 1994, vol. 59, # 16, p. 4461 - 4472]
[23]Yadav; Bandyopadhyay, A; Reddy [Tetrahedron Letters, 2001, vol. 42, # 36, p. 6385 - 6388]
[24]Pu, Xiaotao; Ma, Dawei [Journal of Organic Chemistry, 2006, vol. 71, # 17, p. 6562 - 6572]
[25]Weckerle, Bernhard; Schreier, Peter; Humpf, Hans-Ulrich [Journal of Organic Chemistry, 2001, vol. 66, # 24, p. 8160 - 8164]
[26]Location in patent: body text Nagumo, Shinji; Nakano, Taeko; Hata, Kyomi; Mizukami, Megumi; Miyashita, Masaaki [Organic Letters, 2010, vol. 12, # 5, p. 908 - 911]
[27]Dumpala, Mohan; Kadari, Lingaswamy; Krishna, Palakodety Radha [Synthetic Communications, 2018, vol. 48, # 18, p. 2403 - 2408]

15
[ 928-95-0 ]
[ 89321-71-1 ]
[ 92418-71-8 ]

Yield	Reaction Conditions	Operation in experiment
40%	With tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate In dichloromethane at -20℃; for 48h;	17 Example 17 Example 17 An amount of 500 mg of the solid prepared in Example 4-b, exhibiting a content by mass of tantalum of 5.40% (149 μmol of Ta), is placed in a 100 ml round-bottomed flask with 40 ml of solvent (CH2Cl2). The combined mixture is cooled to 0° C., 31 mg of diethyl (+)-tartrate (160 μmol) are introduced and the mixture is left to stir at 0° C. for 15 hours. 400 mg of trans-2-hexen-1-ol (4.0 mmol) are then added and, 30 minutes later, 1.6 ml of a 6.0M solution of TBHP in dichloromethane (9.6 mmol). The medium is left for 48 hours at 0° C. in order for the epoxidation reaction to take place. The medium is filtered through a sintered glass under argon, the solid catalyst is washed four times with dichloromethane at ambient temperature and the solutions are combined together. Analysis by GC gives a propyloxiranemethanol yield of 14%, a conversion of the trans-2-hexen-1-ol of 25%, i.e. a selectivity of 56%, and an enantiomeric excess of 40% (predominantly (S,S)-propyloxiranemethanol).
	With L-(+)-diisopropyl tartrate; dihydrogen peroxide In dichloromethane at -20 - -15℃; for 3.5h; other primary allyl alcohols, (+)-diethyl tartrate; enantioselectivity;
	With titanium(IV) isopropylate; tert.-butylhydroperoxide In dichloromethane at -20℃; for 3h; other catalysts;

	With titanium(IV) isopropylate; tert.-butylhydroperoxide; 4 A molecular sieve; C₈-poly(L-(+)-tartrate ester) In 2,2,4-trimethylpentane; dichloromethane at -20℃; for 6h; other trans-allylic alcohols, var. ratios of polymer-ligand:titanium, var. temp. and time;
	With L-(+)-diisopropyl tartrate; dihydrogen peroxide In dichloromethane at -20 - -15℃; for 3.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
	With titanium(IV) isopropylate; tert.-butylhydroperoxide; dimethylsulfide; (+)-Weinsaeure-diethylester 1) CH₂Cl₂, 1,2-dichloroethane, -23 deg C, 22 h; 2) 45 min; Yield given. Multistep reaction;
	With tert.-butylhydroperoxide; Diethyl tartrate In dichloromethane at -20℃; for 3h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
	With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate In 2,2,4-trimethylpentane; dichloromethane at -20 - -15℃; for 2.5h; 4 Angstroem molecular sieves; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
	With titanium(IV) isopropylate; tert.-butylhydroperoxide; d-tartrate ^(2-) In dichloromethane at -20℃; for 14h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
	With titanium(IV) isopropylate; tert.-butylhydroperoxide; dimethyl L-tartrate; di-tert-butyl peroxide In dichloromethane 1.) -23 deg C, overnight, 2.) RT, 1 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
	With titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate In dichloromethane at -20℃; for 24h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
	With titanium(IV) isopropylate; tert.-butylhydroperoxide; dimethyl L-tartrate In dichloromethane at -30℃; for 3h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
	With titanium(IV) isopropylate; tert.-butylhydroperoxide; 4 A molecular sieve; C₈-poly(L-(+)-tartrate ester) In 2,2,4-trimethylpentane; dichloromethane at -20℃; for 6h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
	With titanium(IV) isopropylate; tert.-butylhydroperoxide; 4 A molecular sieve; D-(-)-diisopropyl tartrate In dichloromethane at -20℃; for 3h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
	With oxone; ethylenediaminetetraacetic acid; sodium hydrogencarbonate; 1,2,4,5-di-O-isopropylidene-D-erythro-2,3-hexodiuro-2,6-pyranose In acetonitrile at 0℃; for 2h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
	With Oxone; tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate In acetate buffer; acetonitrile at -10℃; for 3h; Title compound not separated from byproducts;
	With tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; 3 A molecular sieve In dichloromethane at 0℃; for 48h;
	With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate at -23℃;
	With titanium(IV) isopropylate; tert.-butylhydroperoxide; polyethyleneglycol monomethyl ether L-(+)-tartrate In 2,2,4-trimethylpentane; dichloromethane at -20℃; for 5h;
	Title compound not separated from byproducts;
	With titanium(IV) isopropylate; tert.-butylhydroperoxide; 4 A molecular sieve In 2,2,4-trimethylpentane; dichloromethane at -20℃; for 8h;
	With (R,R)-N-[2-(diphenylacetylhydroxyamino)cyclohexyl]-N-hydroxy-2,2-diphenylacetamide; tert.-butylhydroperoxide; vanadium(V) oxytriisopropoxide In dichloromethane at 0℃; for 12h;
	With tert.-butylhydroperoxide; oxovanadium(IV) sulfate; (S)-Ph₂CHN(OH)COC(Ph)NHTs In methanol at 0℃; for 20h; Title compound not separated from byproducts;
	With tert.-butylhydroperoxide In dichloromethane at -20℃; for 72h; Title compound not separated from byproducts.;
55 % ee	With tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate In dichloromethane at -20℃; for 48h; Molecular sieve;	14.b Example 14 14-b The same reaction was repeated but this time it was carried out in a homogeneous medium and by using 114 mg of tantalum pentaethoxide (281 μmol) instead of the solid prepared by sublimation of this same compound onto silica, with approximately 250 mg of powdered zeolite 3 , 50 ml of dichloromethane and 0.3 ml of a 1.0M solution of diethyl (+)-(R,R)-tartrate (300 μmol) in dichloromethane. The combined mixture is stirred in a 250 ml round-bottomed flask for 4 hours at -20° C. 535 mg of trans-2-hexen-1-ol (5.35 mmol) and then, 30 minutes later, 2.5 ml of a 5.0M solution of TBHP in dichloromethane (12.5 mmol), which solution is dried beforehand over a 3 sieve, are subsequently introduced successively. This corresponds to a Ta/allyl alcohol molar ratio of approximately 5/100. The combined mixture is left to stir for 48 hours at -20° C. in order for the epoxidation reaction to take place. Analysis by GC gives a propyloxiranemethanol yield of 23%, a conversion of the trans-2-hexen-1-ol of 50%, i.e. a selectivity of 46%, and an enantiomeric excess of 55% (predominantly (R,R)-propyloxiranemethanol), in contrast to Example 14-a using a solid catalyst, for which it is the (S,S) isomer of propyloxiranemethanol which is selectively obtained).
	With C₁₂₀H₉₆N₄Nb₂O₇; urea hydrogen peroxide adduct In toluene at 40℃; for 24h; optical yield given as %ee; enantioselective reaction;
	With titanium(IV) isopropylate; tert.-butylhydroperoxide; C₂₀H₃₈O₈ In dichloromethane at -20℃; for 15h; Molecular sieve; optical yield given as %ee; enantioselective reaction;
	With C₁₂₀H₉₂N₄Nb₂O₇; dihydrogen peroxide; urea In methanol at 40℃; for 24h; optical yield given as %ee; enantioselective reaction;
88 % ee	With tert.-butylhydroperoxide; N,N-Diisopropyltryptamine; titanium(IV)isopropoxide In dichloromethane at -20℃; for 10h; Inert atmosphere; Molecular sieve; Overall yield = 74 %; Overall yield = 429 mg;

Reference： [1]Current Patent Assignee: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE - US6642170, 2003, B1 Location in patent: Page/Page column 20
[2]Choudary, B. M.; Valli, V. L. K.; Prasad, A. Durga [Journal of the Chemical Society. Chemical communications, 1990, # 17, p. 1186 - 1187]
[3]Canali, Laetitia; Karjalainen, Jaana K.; Sherrington, David C.; Hormi, Osmo [Chemical Communications, 1997, # 1, p. 123 - 124]
[4]Karjalainen; Hormi; Sherrington [Tetrahedron Asymmetry, 1998, vol. 9, # 9, p. 1563 - 1575]
[5]Choudary, B. M.; Valli, V. L. K.; Prasad, A. Durga [Journal of the Chemical Society. Chemical communications, 1990, # 17, p. 1186 - 1187]
[6]Gorthey, Lee Ann; Vairamani, Mariappanadar; Djerassi, Carl [Journal of Organic Chemistry, 1984, vol. 49, # 9, p. 1511 - 1517]
[7]Brunner, Henri; Sicheneder, Adolf [Angewandte Chemie, 1988, vol. 100, # 5, p. 730 - 731]
[8]Gao, Yun; Hanson, Robert M.; Klunder, Janice M.; Ko, Soo Y.; Masamune, Hiroko; Sharpless, K. Barry [Journal of the American Chemical Society, 1987, vol. 109, # 19, p. 5765 - 5780]
[9]Mulzer, Johann; Lammer, Ortrud [Chemische Berichte, 1986, vol. 119, # 7, p. 2178 - 2190]
[10]Ferraboschi; Santaniello; Tingoli; Aragozzini; Molinari [Tetrahedron Asymmetry, 1993, vol. 4, # 8, p. 1931 - 1940]
[11]Nakagawa, Naoshi; Mori, Kenji [Agricultural and Biological Chemistry, 1984, vol. 48, # 10, p. 2505 - 2510]
[12]Canali, Laetitia; Karjalainen, Jaana K.; Sherrington, David C.; Hormi, Osmo [Chemical Communications, 1997, # 1, p. 123 - 124]
[13]Karjalainen; Hormi; Sherrington [Tetrahedron Asymmetry, 1998, vol. 9, # 9, p. 1563 - 1575]
[14]Schroeder, Frank; Fettkoether, Regina; Noldt, Uwe; Dettner, Konrad; Koenig, Wilfried A.; Francke, Wittko [Liebigs Annalen der Chemie, 1994, # 12, p. 1211 - 1218]
[15]Tu, Yong; Wang, Zhi-Xian; Shi, Yian [Journal of the American Chemical Society, 1996, vol. 118, # 40, p. 9806 - 9807]
[16]Wang, Zhi-Xian; Shi, Yian [Journal of Organic Chemistry, 1998, vol. 63, # 9, p. 3099 - 3104]
[17]Meunier, Damien; Piechaczyk, Arnaud; De Mallmann, Aimery; Basset, Jean-Marie [Angewandte Chemie - International Edition, 1999, vol. 38, # 23, p. 3540 - 3542]
[18]Mukaiyama, Teruaki; Arai, Hidehiro; Shiina, Isamu [Chemistry Letters, 2000, # 5, p. 580 - 581]
[19]Guo, Hongchao; Shi, Xueyan; Qiao, Zhen; Hou, Shicong; Wang, Min [Chemical Communications, 2002, # 2, p. 118 - 119]
[20]Fringuelli, Francesco; Pizzo, Ferdinando; Rucci, Mauro; Vaccaro, Luigi [Journal of Organic Chemistry, 2003, vol. 68, # 18, p. 7041 - 7045]
[21]Guo, Hong-Chao; Shi, Xue-Yan; Wang, Xian; Liu, Shang-Zhong; Wang, Min [Journal of Organic Chemistry, 2004, vol. 69, # 6, p. 2042 - 2047]
[22]Zhang, Wei; Basak, Arindrajit; Kosugi, Yuji; Hoshino, Yujiro; Yamamoto, Hisashi [Angewandte Chemie - International Edition, 2005, vol. 44, # 28, p. 4389 - 4391]
[23]Bourhani, Zainaba; Malkov, Andrei V. [Chemical Communications, 2005, # 36, p. 4592 - 4594]
[24]Barlan, Allan U.; Zhang, Wei; Yamamoto, Hisashi [Tetrahedron, 2007, vol. 63, # 27, p. 6075 - 6087]
[25]Current Patent Assignee: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE - US6642170, 2003, B1 Location in patent: Page/Page column 19
[26]Location in patent: experimental part Egami, Hiromichi; Katsuki, Tsutomu [Angewandte Chemie - International Edition, 2008, vol. 47, # 28, p. 5171 - 5174]
[27]Location in patent: scheme or table Knight, David W.; Morgan, Ian R. [Tetrahedron Letters, 2009, vol. 50, # 1, p. 35 - 38]
[28]Location in patent: scheme or table Egami, Hiromichi; Oguma, Takuya; Katsuki, Tsutomu [Journal of the American Chemical Society, 2010, vol. 132, # 16, p. 5886 - 5895]
[29]Uesugi, Shun-Ichiro; Watanabe, Tsubasa; Imaizumi, Takamichi; Shibuya, Masatoshi; Kanoh, Naoki; Iwabuchi, Yoshiharu [Organic Letters, 2014, vol. 16, # 17, p. 4408 - 4411]

16
[ 928-95-0 ]
[ 92418-71-8 ]

Yield	Reaction Conditions	Operation in experiment
90%	With tert.-butylhydroperoxide; Ti(O-i-Pr)4; D-(-)-diisopropyl tartrate In dichloromethane; toluene at -25℃; for 2h; Inert atmosphere; Molecular sieve; enantioselective reaction;
80%	With titanium(IV) isopropylate; tert.-butylhydroperoxide; 4 A molecular sieve In dichloromethane at -20℃; for 3h;
79%	With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate In decane; dichloromethane at -25℃; for 3h; Molecular sieve; Inert atmosphere;

71%	With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate In dichloromethane at -20℃;
63%	With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate In dichloromethane
63%	With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate In dichloromethane
60%	Stage #1: (E)-2-Hexen-1-ol With titanium(IV) isopropylate; diethyl (2R,3R)-tartrate In dichloromethane at -78℃; for 0.166667h; Molecular sieve; Stage #2: With Cumene hydroperoxide In dichloromethane at -78 - -20℃; for 17h; Molecular sieve;
50%	With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate
48%	Stage #1: (E)-2-Hexen-1-ol In dichloromethane at -20℃; for 0.5h; Molecular sieve; Stage #2: With tert.-butylhydroperoxide In dichloromethane at -20℃; for 4h;	1 Add trans-2-hexen-l-ol (12 mL, 102 mmol), (-) -diethyl tartrate (2.1 mL, 12.3 mmol), and Ti (OPr) 4 (3.0 mL, 10.2 mmol) to a cooled (-20°C) solution of activated, dried, crushed 4A molecular sieves (50 g) in dichloromethane (700 mL). After 30 minutes, add a dry [JACS, 1987, 109, 5765] solution of t-BuOOH in dichloromethane (-5M in dichloromethane, 57 mL, 285 mmol). Stir for 4 hours at-20°C and filter the solids. Add 700 mL of 15% L-tartartic acid to the filtrate and stir for 20 minutes. Separate the layers, extract the aqueous layer with dichloromethane, and concentrate the combined organic extracts in vacuo. Add 300 mL diethyl ether to residue and cool to 0°C. Add cool (0°C) 15% NaOH, stir for 15 minutes, separate, and extract aqueous layer with diethyl ether. Wash the organic layer with aqueous saturated sodium chloride, dry over anhydrous MgSO¢, filter, and concentrate in vacuo. Purify on silica gel eluting with 0-50% EtOAc/hexanes to give (2R, 3R)- (3-propyl-oxiranyl)-methanol (5.69 g, 48%). 1H NMR (CDC13) 6 3.97-3. 88 (m, 1H), 3.68-3. 59 (m, 1H), 3.00-2. 91 (m, 2H), 1.83-1. 68 (m, 1H), 1.61-1. 41 (m, 4H), 0.97 (t, 3H).
	With titanium(IV) isopropylate; tert.-butylhydroperoxide; molecular sieve; diethyl (2S,3S)-tartrate In 2,2,4-trimethylpentane; dichloromethane at -20℃; for 48h;
	With titanium(IV) isopropylate; tert.-butylhydroperoxide; chiral DET
	With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate In dichloromethane at -30℃; for 72h;
	With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate In dichloromethane at -30℃; for 72h;
	With titanium(IV) isopropylate; tert.-butylhydroperoxide; (+)-Weinsaeure-diethylester
94 % ee	With diethyl (2S,3S)-tartrate; Cumene hydroperoxide; titanium(IV)isopropoxide In dichloromethane at -15 - 0℃; for 1.83333h; Molecular sieve; Inert atmosphere;	1 Synthesis of (3R-trans)-(3-propyloxyranyl)methanol (V) Example 1 Synthesis of (3R-trans)-(3-propyloxyranyl)methanol (V) MS 4 Å (7.5 g, D-(-)-diethyltartrate (3.1 g, 15 mmol) and cumene hydroperoxide (80% w/w, 95 g, 500 mmol) are added in sequence to a solution of Ti(OiPr)4 (3.55 g, 12.5 mmol) in dichloromethane (375 ml) cooled to -20° C. under inert atmosphere, and the temperature is maintained below -15° C. After 30 minutes a solution of trans-2-hexen-1-ol (25 g, 250 mmol) in dichloromethane (125 ml) is added in 20 minutes, and the temperature is maintained below -15° C. After 90 minutes the reaction mixture is heated to 0° C. and water (70 ml) is added, while maintaining the mixture under vigorous stirring. An NaOH solution (30%, 15 ml) is added to the mixture after 45 minutes, and the mixture is stirred vigorously for 30 minutes, after which the phases are separated. The aqueous phase is extracted twice with 50 ml of dichloromethane, and the combined organic phases are treated with a saturated solution of sodium thiosulphate (200 ml) for 30 minutes. The phases are separated and the organic phase is treated with a saturated solution of sodium chloride, dried on sodium sulphate, filtered and concentrated at low pressure until crude (3R-trans)-(3-propyloxyranyl)methanol of formula (V) is obtained, which is not purified but used "as is" in the next reaction. A portion of the crude product is purified by flash chromatography for analysis purposes. The chemically pure sample thus obtained was analysed by NMR spectroscopy, and perfectly agreed with the structure. The same sample was also derivatised as Mosher ester and analysed by gas chromatography; it proved chemically pure, with an enantiomeric excess of 94%. 1H-NMR, (CDCl3) δ: 3.92 (dd, 1H, J=2.7, 12.8 Hz), 3.63 (dd, 1H, J=4.5, 12.8 Hz), 2.9-3.0 (m, 2H), 1.4-1.6 (m, 4H), 0.94 (t, 3H, J=8 Hz).
	With titanium(IV) isopropylate; diethyl (2S,3S)-tartrate; Cumene hydroperoxide In dichloromethane at -20 - -15℃; for 1.83333h; Molecular sieve; Inert atmosphere;	1 Example 1 - Synthesis of (3R-trans)-(3-propyloxyranyl)methanol (V) Example 1 - Synthesis of (3R-trans)-(3-propyloxyranyl)methanol (V) [0089] MS 4 Å (7.5 g, D-(-)-diethyltartrate (3.1 g, 15 mmol) and cumene hydroperoxide (80% w/w, 95 g, 500 mmol) are added in sequence to a solution of Ti(OiPr)4 (3.55 g, 12.5 mmol) in dichloromethane (375 ml) cooled to -20°C under inert atmosphere, and the temperature is maintained below -15°C. After 30 minutes a solution of trans-2-hexen-1-ol (25 g, 250 mmol) in dichloromethane (125 ml) is added in 20 minutes, and the temperature is maintained below -15°C. After 90 minutes the reaction mixture is heated to 0°C and water (70 ml) is added, while maintaining the mixture under vigorous stirring. An NaOH solution (30%, 15 ml) is added to the mixture after 45 minutes, and the mixture is stirred vigorously for 30 minutes, after which the phases are separated. The aqueous phase is extracted twice with 50 ml of dichloromethane, and the combined organic phases are treated with a saturated solution of sodium thiosulphate (200 ml) for 30 minutes. The phases are separated and the organic phase is treated with a saturated solution of sodium chloride, dried on sodium sulphate, filtered and concentrated at low pressure until crude (3R-trans)-(3-propyloxyranyl)methanol of formula ( V) is obtained, which is not purified but used "as is" in the next reaction.
100 % de	With tert.-butylhydroperoxide In dichloromethane at 54.84℃; for 24h; diastereoselective reaction;	3 3.11. Catalytic studies General procedure: The materials were tested as catalysts in the epoxidationof olefins and allylic alcohols, such as cis-cyclooctene, styrene,1-octene, trans-hex-2-en-1-ol, cis-3-hex-1-ol, geraniol, and R-(+)-limonene, using t-butylhydroperoxide (tbhp) as oxidant (Aldrich,5.5 M in decane). The catalytic oxidation tests were carried out at328 K under air in a vessel equipped with a magnetic stirrer anda condenser. In a typical experiment, the vessel was loaded witholefin or alcohol (100%), internal standard (dibutyl ether, DBE),catalyst (175 mg), oxidant (200%), and 3 mL of dichloromethaneas solvent. The final volume of the reaction was ca. 6 mL. Addi-tion of the oxidant determined the initial time of the reaction.Conversion, product yields and stereochemistry were monitoredby sampling periodically and analyzing them using a ShimadzuQP2100-Plus GC/MS system and a capillary column (TeknokromaTRB-5MS/TRB-1MS or Restek Rt-DEXsm) operating in the lin-ear velocity mode. Leaching and recycling experiments, in general,were carried out as described above for trans-hex-2-en-1-ol epox-idation using material Si16-pyca-2 and Si16-pyca-1 as catalyst;conversion and product yields were monitored as described above.For the leaching experiments after 2 h reaction, the catalyst wasfiltered off, and the reactions continued under the same conditions.In the case of the recycling experiments, after each cycle (24 h),the catalyst was filtered, washed with dichloromethane, and driedprior to reuse in a new catalytic cycle.

Reference： [1]Location in patent: experimental part Srihari, Pabbaraja; Kumaraswamy, Boyapelly; Rao, Gokada Maheswara; Yadav, Jhillu Singh [Tetrahedron Asymmetry, 2010, vol. 21, # 1, p. 106 - 111]
[2]Perez, Alice L.; Gries, Gerhard; Gries, Regine; Giblin-Davis, Robin M.; Oehlschlager, A. Cameron [Journal of Chemical Ecology, 1994, vol. 20, # 10, p. 2653 - 2672]
[3]Schubert, Christopher P. J.; Müller, Carsten; Wand, Michael D.; Giesselmann, Frank; Lemieux, Robert P. [Chemical Communications, 2015, vol. 51, # 63, p. 12601 - 12604]
[4]Iwama, Seiji; Segawa, Masaki; Fujii, Shinobu; Ikeda, Kiyoshi; Katsumura, Shigeo [Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 24, p. 3495 - 3498]
[5]Rayner, Christopher M.; Westwell, Andrew D. [Tetrahedron Letters, 1992, vol. 33, # 17, p. 2409 - 2412]
[6]Rayner; Sin; Westwell [Tetrahedron Letters, 1992, vol. 33, # 47, p. 7237 - 7240]
[7]Diamandas, Matthew; Moreira, Ryan; Taylor, Scott D. [Organic Letters, 2021, vol. 23, # 8, p. 3048 - 3052]
[8]Thijs, Lambertus; Waanders, Peter P.; Stokkingreef, Edwin H. M.; Zwanenburg, Binne [Recueil des Travaux Chimiques des Pays-Bas, 1986, vol. 105, p. 332 - 337]
[9]Current Patent Assignee: ELI LILLY & CO - WO2005/92835, 2005, A1 Location in patent: Page/Page column 20
[10]Ghosh, Arun K.; Lee, Hee Yoon; Thompson, Wayne J.; Culberson, Chris; Holloway, M. Katharine; et al. [Journal of Medicinal Chemistry, 1994, vol. 37, # 8, p. 1177 - 1188]
[11]Pu, Xiaotao; Ma, Dawei [Journal of Organic Chemistry, 2006, vol. 71, # 17, p. 6562 - 6572]
[12]Pickenhagen, Wilhelm; Broenner-Schindler, Helene [Helvetica Chimica Acta, 1984, vol. 67, p. 947 - 952]
[13]Weckerle, Bernhard; Schreier, Peter; Humpf, Hans-Ulrich [Journal of Organic Chemistry, 2001, vol. 66, # 24, p. 8160 - 8164]
[14]Wu, Yen-Ku; Liu, Hsing-Jang; Zhu, Jia-Liang [Synlett, 2008, # 4, p. 621 - 623]
[15]Current Patent Assignee: DIPHARMA FRANCIS S.R.L. - US2014/148574, 2014, A1 Location in patent: Paragraph 0104; 0105; 0106
[16]Current Patent Assignee: DIPHARMA FRANCIS S.R.L. - EP2738164, 2014, A1 Location in patent: Paragraph 0089
[17]Saraiva, Marta S.; Fernandes, Cristina I.; Nunes, Teresa G.; Calhorda, Maria José; Nunes, Carla D. [Applied Catalysis A: General, 2015, vol. 504, p. 328 - 337]
[18]Mopuri, Sudhakar Reddy; Palakodety, Radha Krishna [Tetrahedron Letters, 2019, vol. 60, # 34]

17
[ 928-95-0 ]
[ 108-24-7 ]
[ 2497-18-9 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 825 - 829
[2]Chemistry - A European Journal,2015,vol. 21,p. 7030 - 7034
[3]Journal of the American Chemical Society,2007,vol. 129,p. 14172 - 14173
[4]Journal of Organic Chemistry,2013,vol. 78,p. 1559 - 1575
[5]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1983,vol. 22,p. 919 - 920
[6]Angewandte Chemie - International Edition,2008,vol. 47,p. 1928 - 1931
[7]Organic Letters,2012,vol. 14,p. 1416 - 1419

18
[ 928-95-0 ]
[ 100-39-0 ]
[ 146330-81-6 ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: (E)-2-Hexen-1-ol With sodium hydride In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: benzyl bromide In tetrahydrofuran at 0 - 20℃; for 16h; Inert atmosphere;
	With sodium hydride 1) mineral oil, THF, 50 deg C, 2) THF, 50-60 deg C, 18 h; Yield given. Multistep reaction;
	With sodium hydride 1.) THF, RT, 15 min, 2.) THF, RT, overnight; Yield given. Multistep reaction;

Reference： [1]Pérez, Manuel; Fañanás-Mastral, Martín; Hornillos, Valentín; Rudolph, Alena; Bos, Pieter H.; Harutyunyan, Syuzanna R.; Feringa, Ben L. [Chemistry - A European Journal, 2012, vol. 18, # 38, p. 11880 - 11883]
[2]Chini, Marco; Crotti, Paolo; Flippin, Lee A.; Gardelli, Christina; Giovani, Elena; et al. [Journal of Organic Chemistry, 1993, vol. 58, # 5, p. 1221 - 1227]
[3]Crich, David; Beckwith, Athelstan L. J.; Chen, Chen; Yao, Qingwei; Davison, Ian G. E.; Longmore, Robert W.; De Parrodi, Cecilia Anaya; Quintero-Cortes, Leticia; Sandoval-Ramirez, Jésus [Journal of the American Chemical Society, 1995, vol. 117, # 34, p. 8757 - 8768]

19
[ 928-95-0 ]
[ 814-49-3 ]
[ 103896-62-4 ]

Yield	Reaction Conditions	Operation in experiment
91%	With 1-methyl-1H-imidazole In dichloromethane at 20℃; for 13h;
73%	With pyridine; dmap In dichloromethane at 0 - 20℃; Inert atmosphere;
	With pyridine In dichloromethane for 2h; Ambient temperature;

	With pyridine; dmap In dichloromethane at 0 - 20℃; Schlenk technique; Inert atmosphere;
	With pyridine; dmap In dichloromethane at 0 - 20℃; Inert atmosphere;

Reference： [1]Kawashima, Hidehisa; Ogawa, Narihito; Saeki, Ryohei; Kobayashi, Yuichi [Chemical Communications, 2016, vol. 52, # 27, p. 4918 - 4921]
[2]Bag, Sukdev; Dutta, Uttam; Jayarajan, Ramasamy; Maiti, Debabrata; Mondal, Arup; Porey, Sandip; Sunoj, Raghavan B.; Surya, K. [Journal of the American Chemical Society, 2020, vol. 142, # 28, p. 12453 - 12466]
[3]Murahashi, Shun-Ichi; Taniguchi, Yuki; Imada, Yasushi; Tanigawa, Yoshio [Journal of Organic Chemistry, 1989, vol. 54, # 14, p. 3292 - 3303]
[4]Zhang, Zhen-Qi; Zhang, Ben; Lu, Xi; Liu, Jing-Hui; Lu, Xiao-Yu; Xiao, Bin; Fu, Yao [Organic Letters, 2016, vol. 18, # 5, p. 952 - 955]
[5]Zhang, Zhen-Qi; Zhang, Ben; Lu, Xi; Liu, Jing-Hui; Lu, Xiao-Yu; Xiao, Bin; Fu, Yao [Organic Letters, 2016, vol. 18, # 5, p. 952 - 955]

20
[ 928-95-0 ]
[ 124-63-0 ]
[ 99704-81-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine In dichloromethane at -15℃; for 1h; Green chemistry;
100%	With triethylamine In dichloromethane at -15℃; for 1.5h;
99%	With triethylamine In tetrahydrofuran at 0℃; for 3h;

94%	With triethylamine In tetrahydrofuran at 0℃;
	With triethylamine In dichloromethane for 1h; Ambient temperature;
	With triethylamine In diethyl ether
	With triethylamine In dichloromethane at 0 - 25℃; for 2h; Inert atmosphere;
	With triethylamine In tetrahydrofuran at 0 - 20℃; for 1h;	A typical one-pot preparation of sulfide 3 (entry 1 in Table 1) General procedure: To a solution of n-pentanol (0.440 g, 5.0 mmol) in THF (20.0 mL) at 0 C were added methansulfonyl chloride (0.465 mL, 6.0 mmol) and triethylamine (0.906 mL, 6.5 mmol). After the mixture was stirred at RT for 1.5 h, a solution of 5-mercapto-1-phenyl-1H-tetrazole (0.891 g, 5.0 mmol) and NaH (0.46 g, 11.5 mmol) in THF (5.0 mL) was added at 0 C. The resulting mixture was stirred at RT for 16 h. The reaction was quenched with sat. NH4Cl aq., and the mixture was extracted with AcOEt (3 10 mL). The combined extracts were washed with brine, dried (MgSO4), and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hex:AcOEt = 8:1) to afford 3a (1.076 g, 86%) as a colorless oil. 1 H NMR (400 MHz, CDCl3) d 0.91 (3H, t, J = 7.3 Hz), 1.31-1.47 (4H, m), 1.83 (2H, quin, J = 7.3 Hz), 3.40 (2H, t, J = 7.3 Hz), 7.51-7.61 (5H, m) [16].

Reference： [1]Olivito; Costanzo; Di Gioia; Nardi; Oliverio; Procopio [Organic and Biomolecular Chemistry, 2018, vol. 16, # 41, p. 7753 - 7759]
[2]Olivito, Fabrizio; Amodio, Nicola; Di Gioia, Maria Luisa; Nardi, Monica; Oliverio, Manuela; Juli, Giada; Tassone, Pierfrancesco; Procopio, Antonio [MedChemComm, 2019, vol. 10, # 1, p. 116 - 119]
[3]Hiroi, Kunio; Makino, Kunitaka [Chemical and pharmaceutical bulletin, 1988, vol. 36, # 5, p. 1727 - 1737]
[4]Merten, Sandra; Froehlich, Roland; Kataeva, Olga; Metz, Peter [Advanced Synthesis and Catalysis, 2005, vol. 347, # 6, p. 754 - 758]
[5]Cardillo, Giuliana; Orena, Mario; Penna, Maurizio; Sandri, Sergio; Tomasini, Claudia [Tetrahedron, 1991, vol. 47, # 12-13, p. 2263 - 2272]
[6]Dussault; Eary [Journal of the American Chemical Society, 1998, vol. 120, # 28, p. 7133 - 7134]
[7]Cheng, Yi An; Yu, Wesley Zongrong; Yeung, Ying-Yeung [Angewandte Chemie - International Edition, 2015, vol. 54, # 41, p. 12102 - 12106][Angew. Chem., 2015, vol. 54, p. 12102 - 12106,5]
[8]Ando, Kaori; Hattori, Junichiro [Tetrahedron Letters, 2019, vol. 60, # 36]

21
[ 928-95-0 ]
[ 1079-66-9 ]
C₁₈H₂₁OP [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine In diethyl ether for 1h; Ambient temperature;
	With triethylamine In dichloromethane at 20℃; for 2h; Inert atmosphere;	4.2. General procedure for the preparation of 2-thio-substituted benzothiazoles General procedure: To a stirred solution of alcohol (1 mmol), Et3N (1.2 equiv.) in dry CH2Cl2 (1 mL) was successively added chlorodiphenylphosphine (1.2 equiv.) at RT under N2 atmosphere. After 2 h, benzothiazole-2-thiol (0.5 equiv.) and camphorquinone (1 equiv.) were added to the mixture, respectively. After the mixture was stirred for 12 h, it was extracted with CH2Cl2/H2O. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by preparative TLC on silica gel (hexane/EtOAc = 10/1) to afford the desired product.

Reference： [1]Armstrong, Susan K.; Collington, Eric W.; Knight, Julian G.; Naylor, Alan; Warren, Stuart [Journal of the Chemical Society. Perkin transactions I, 1993, # 13, p. 1433 - 1448]
[2]Pluempanupat, Wanchai; Temyarasilp, Parinthorn; Widhalm, Michael; Chavasiri, Warinthorn [Journal of Sulfur Chemistry, 2014, vol. 35, # 4, p. 418 - 430]

22
[ 928-95-0 ]
[ 545-06-2 ]
[ 51479-70-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 2h;
95%	With potassium hydroxide; tetrabutylammonium hydrogensulfate In dichloromethane at -15 - 25℃; for 1h;
86%	With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 2h; Inert atmosphere;

	With sodium hydride 1.) THF, 0 deg C, 1 h, 2.) THF, 1.5 h, RT; Yield given. Multistep reaction;
	With sodium hydride 1.) THF, 0 deg C, 1 h, 2.) THF, RT, 1.5 h; Multistep reaction;
	With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 4℃; for 0.1h;

Reference： [1]Olson, Angela C.; Overman, Larry E.; Sneddon, Helen F.; Ziller, W. Joseph [Advanced Synthesis and Catalysis, 2009, vol. 351, # 18, p. 3186 - 3192]
[2]Patil, Vijay J. [Tetrahedron Letters, 1996, vol. 37, # 9, p. 1481 - 1484]
[3]Demircan, Aysegül; Heberle, Martin; Peters, René; Pfeffer, Camilla; Wannenmacher, Nick; Wanner, Daniel M.; Yu, Xin [Advanced Synthesis and Catalysis, 2022]
[4]Bongini, Alessandro; Cardillo, Giuliana; Orena, Mario; Sandri, Sergio; Tomasini, Claudia [Journal of Organic Chemistry, 1986, vol. 51, # 25, p. 4905 - 4910]
[5]Cardillo; Orena; Sandri [Journal of Organic Chemistry, 1986, vol. 51, # 5, p. 713 - 717]
[6]Anderson, Carolyn E.; Overman, Larry E.; Watson, Mary P.; Maddess, Matthew L.; Lautens, Mark [Organic Syntheses, 2005, vol. 82, p. 134 - 139]

23
[ 928-95-0 ]
[ 98-59-9 ]
[ 205882-94-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With n-butyllithium In tetrahydrofuran; hexane at -80℃; for 48h;
	With n-butyllithium 1) hexane, THF, -78 deg C, 2) -78 deg C, 72 h; Multistep reaction;
	With potassium hydroxide

Reference： [1]Fiedler, Dorothea; Bergman, Robert G.; Raymond, Kenneth N. [Angewandte Chemie - International Edition, 2004, vol. 43, # 48, p. 6748 - 6751] Fiedler, Dorothea; Van Halbeek, Herman; Bergman, Robert G.; Raymond, Kenneth N. [Journal of the American Chemical Society, 2006, vol. 128, # 31, p. 10240 - 10252]
[2]Barta, Nancy S.; Cook, Gregory R.; Landis, Margaret S.; Stille, John R. [Journal of Organic Chemistry, 1992, vol. 57, # 28, p. 7188 - 7194]
[3]Tsukada, Naofumi; Sugawara, Shuichi; Okuzawa, Tomohiro; Inoue, Yoshio [Synthesis, 2006, # 18, p. 3003 - 3008]

24
[ 928-95-0 ]
[ 5394-63-8 ]
[ 169393-22-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	In xylene at 150℃; for 0.5h;

Reference： [1]Doyle, Michael P.; Austin, Richard E.; Bailey, A. Scott; Dwyer, Michael P.; Dyatkin, Alexey B.; Kalinin, Alexey V.; Kwan, Michelle M. Y.; Liras, Spiros; Oalmann, Christopher J.; Pieters, Roland J.; Protopopova, Marina N.; Raab, Conrad E.; Roos, Gregory H. P.; Zhou, Qi-Lin; Martin, Stephen F. [Journal of the American Chemical Society, 1995, vol. 117, # 21, p. 5763 - 5775]

25
[ 928-95-0 ]
[ 74-88-4 ]
[ 56052-83-6 ]

Yield	Reaction Conditions	Operation in experiment
75%	With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 2h;
	With sodium hydride 1.) THF, 30 min, 2.) THF, reflux, 30 min; Yield given. Multistep reaction;
	With sodium hydride In tetrahydrofuran

	Stage #1: (E)-2-Hexen-1-ol With sodium hydride In Triethylene glycol dimethyl ether Stage #2: methyl iodide
	Stage #1: (E)-2-Hexen-1-ol With sodium hydride In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran at 0 - 20℃; for 16h; Inert atmosphere;
	With sodium hydride In N,N-dimethyl-formamide at 20℃;

Reference： [1]Park, Sae Rom; Kim, Cheoljae; Kim, Dong-Gil; Thrimurtulu, Neetipalli; Yeom, Hyun-Suk; Jun, Jungho; Shin, Seunghoon; Rhee, Young Ho [Organic Letters, 2013, vol. 15, # 6, p. 1166 - 1169]
[2]Crich, David; Beckwith, Athelstan L. J.; Chen, Chen; Yao, Qingwei; Davison, Ian G. E.; Longmore, Robert W.; De Parrodi, Cecilia Anaya; Quintero-Cortes, Leticia; Sandoval-Ramirez, Jésus [Journal of the American Chemical Society, 1995, vol. 117, # 34, p. 8757 - 8768]
[3]Van De Waal, Matthijs; Niclass, Yvan; Snowden, Roger L.; Bernardinelli, Geerald; Escher, Sina [Helvetica Chimica Acta, 2002, vol. 85, # 5, p. 1246 - 1260]
[4]Location in patent: scheme or table Bowen, Richard D.; Edwards, Howell G.M.; Farwell, Dennis W. [Journal of Molecular Structure, 2010, vol. 976, # 1-3, p. 36 - 41]
[5]Pérez, Manuel; Fañanás-Mastral, Martín; Hornillos, Valentín; Rudolph, Alena; Bos, Pieter H.; Harutyunyan, Syuzanna R.; Feringa, Ben L. [Chemistry - A European Journal, 2012, vol. 18, # 38, p. 11880 - 11883]
[6]Phipps, Erik J.T.; Rovis, Tomislav [Journal of the American Chemical Society, 2019, vol. 141, # 17, p. 6807 - 6811]

26
[ 928-95-0 ]
[ 14399-53-2 ]
(2-propylcyclopropyl) methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With titanium tetrachloride In dichloromethane at -20℃;

Reference： [1]Charette, André B.; Brochu, Christian [Journal of the American Chemical Society, 1995, vol. 117, # 45, p. 11367 - 11368]

27
[ 108-05-4 ]
[ 928-95-0 ]
[ 2497-18-9 ]

Reference： [1]Journal of Organic Chemistry,1996,vol. 61,p. 3088 - 3092

28
[ 928-95-0 ]
[ 79-08-3 ]
[ 175019-14-4 ]

Yield	Reaction Conditions	Operation in experiment
89%	Stage #1: (E)-2-Hexen-1-ol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: bromoacetic acid In tetrahydrofuran; mineral oil Inert atmosphere; Reflux;
	With sodium hydride Yield given. Multistep reaction;
	Stage #1: (E)-2-Hexen-1-ol With sodium hydride In tetrahydrofuran at 20℃; Stage #2: bromoacetic acid In tetrahydrofuran at 20℃;

Stage #1: (E)-2-Hexen-1-ol With sodium hydride In tetrahydrofuran; mineral oil at -78℃; for 0.5h; Inert atmosphere; Stage #2: bromoacetic acid In tetrahydrofuran; mineral oil at -78 - 20℃; for 18h; Inert atmosphere; Further stages;

Reference： [1]Luo, Xiya; Ma, Xiaofeng; Lebreux, Frédéric; Markó, István E.; Lam, Kevin [Chemical Communications, 2018, vol. 54, # 71, p. 9969 - 9972]
[2]Enders, Dieter; Backhaus, Dirk; Runsink, Jan [Tetrahedron, 1996, vol. 52, # 5, p. 1503 - 1528]
[3]Hiersemann [Synthesis, 2000, # 9, p. 1279 - 1290]
[4]Nelson, Bjoern; Hiller, Wolf; Pollex, Annett; Hiersemann, Martin [Organic Letters, 2011, vol. 13, # 16, p. 4438 - 4441]

29
[ 928-95-0 ]
[ 111003-36-2 ]

Yield	Reaction Conditions	Operation in experiment
96%	Stage #1: (E)-2-Hexen-1-ol With titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate In 2,2,4-trimethylpentane; dichloromethane at -20℃; for 12h; Stage #2: With L-Tartaric acid; iron(II) sulfate In 2,2,4-trimethylpentane; dichloromethane; water at 0℃; for 1h;
89%	Stage #1: (E)-2-Hexen-1-ol With titanium(IV) isopropylate; D-(-)-diisopropyl tartrate In dichloromethane at -23℃; for 0.5h; Inert atmosphere; Stage #2: With tert.-butylhydroperoxide In dichloromethane at -23 - 20℃; Inert atmosphere;
	With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; 4 A molecular sieve In 2,2,4-trimethylpentane; dichloromethane 1.) -20 deg C - (-15 deg C), 5 h, 2.) room remperature, 1 h;

With tert.-butylhydroperoxide; (4,4'-dimethyl-2,2'-bipyridine)dichloridodioxidomolybdenum(VI) In decane; dichloromethane at 54.84℃; enantioselective reaction;

2.3 Catalytic tests General procedure: The complexes and materials were tested in the epoxidation of olefins and allylic alcohols, such as cis-cyclooctene, styrene, 1-octene, trans-hex-2-en-1-ol, and R-(+)-limonene, using t-butylhydroperoxide (tbhp) as oxidant (Aldrich, 5.5M in n-decane). The catalytic oxidation tests were carried out at 328K under air in a reaction vessel equipped with a magnetic stirrer and a condenser. In a typical experiment, the vessel was loaded with olefin or alcohol (100mol%), internal standard (dibutyl ether, dbe), catalyst (1mol%), oxidant (200mol%), and 3mL of dichloromethane as solvent. The final volume of the reaction is ca. 6mL. Addition of the oxidant determines the initial time of the reaction. Conversion, product yields and stereochemistry were monitored by sampling periodically and analyzing them using a Shimadzu QP2100-Plus GC/MS system and a capillary column (Teknokroma TRB-5MS/TRB-1MS or Restek Rt-βDEXsm) operating in the linear velocity mode. All reactions were conducted under normal atmosphere. R-(+)-limonene epoxidation was carried out at different temperatures, 328K, 353K, and 393K, using dichloromethane, ethanol, and toluene as solvents, respectively.

Reference： [1]Reed, Neal N.; Dickerson, Tobin J.; Boldt, Grant E.; Janda, Kim D. [Journal of Organic Chemistry, 2005, vol. 70, # 5, p. 1728 - 1731]
[2]Zhang, Fan; Wen, Xiaoan; Xu, Qing-Long; Sun, Hongbin [European Journal of Organic Chemistry, 2014, vol. 2014, # 36, p. 8101 - 8109]
[3]Darcel, Christophe; Bruneau, Christian; Dixneuf, Pierre H.; Roberts, Stanley M. [Tetrahedron, 1997, vol. 53, # 27, p. 9241 - 9252]
[4]Fernandes, Cristina I.; Saraiva, Marta S.; Nunes, Teresa G.; Vaz, Pedro D.; Nunes, Carla D. [Journal of Catalysis, 2014, vol. 309, p. 21 - 32]

30
[ 928-95-0 ]
[ 6728-26-3 ]
[ 106498-75-3 ]

Yield	Reaction Conditions	Operation in experiment
83 % Spectr.	With tert.-butylhydroperoxide; 3 A molecular sieve In 2,2,4-trimethylpentane; cyclohexane Heating;
	With tert.-butylhydroperoxide In decane; toluene at 79.84℃; for 24h;	2.3. Catalytic epoxidation of olefins General procedure: Catalytic tests were carried out in a Carousel 12 Plus ReactionStation from Radleys. A given amount (1.6 mmol) of the olefin substrates- cis-cyclooctene, styrene, 1-octene, trans-2-hexen-1-ol, R-(+)-limonene - was mixed with dibutylether (1.6 mmol) (internalstandard) and 15 μL (5 mol %) of tert-butyl hydroperoxide (5.5M solutionin decane; tbhp). Then the catalyst was added to this mixture.This was either 10 mL of exfoliated materials ExHTCo/Al-met-Au(0.016 mol Au) with an extra 5 mL of acetonitrile or 100 mg of HTCo/Almet-Au (0.016 mol Au) bulk catalyst with 8 mL of toluene. The magneticallystirred mixture was heated to 353 K and kept for 80 h.

Reference： [1]Palombi, Laura; Bonadiesa, Francesco; Scettri, Arrigo [Tetrahedron, 1997, vol. 53, # 46, p. 15867 - 15876]
[2]Leandro, Sónia R.; Fernandes, Cristina I.; Viana; Mourato; Vaz, Pedro D.; Nunes, Carla D. [Applied Catalysis A: General, 2019, vol. 584]

31
[ 928-95-0 ]
[ 100-52-7 ]
[ 175788-33-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	With indium iodide; triphenylphosphine In various solvent(s) at 20℃; for 15h;
96 % Chromat.	With tin(ll) chloride In n-heptane; water at 35℃; for 50h;

Reference： [1]Hirashita, Tsunehisa; Kambe, Shinya; Tsuji, Hiromitsu; Omori, Hideki; Araki, Shuki [Journal of Organic Chemistry, 2004, vol. 69, # 15, p. 5054 - 5059]
[2]Okano, Tamon; Kiji, Jitsuo; Doi, Takanori [Chemistry Letters, 1998, # 1, p. 5 - 6]

32
[ 928-95-0 ]
[ 19689-92-0 ]
[ 2497-18-9 ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 8141 - 8144

33
[ 928-95-0 ]
[ 127-65-1 ]
((2S*,3R*)-3-propyl-1-tosylaziridin-2-yl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With phenyltrimethylammonium tribromide In acetonitrile at 25℃; for 12h;
79%	With iodine; Aliquat 336 at 20℃; for 3h;
66%	With phenyltrimethylammonium tribromide In acetonitrile at 20℃; for 16h; Inert atmosphere;

58%	With iodine; silica gel; potassium carbonate In water at 20℃; for 3h;
	With phenyltrimethylammonium tribromide In acetonitrile at 20℃; for 12h;

Reference： [1]Jeong; Tao; Sagasser; Henniges; Sharpless [Journal of the American Chemical Society, 1998, vol. 120, # 27, p. 6844 - 6845]
[2]Kano, Daisuke; Minakata, Satoshi; Komatsu, Mitsuo [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2001, # 23, p. 3186 - 3188]
[3]Anderson, Edward A.; Mousseau, James. J.; Nugent, Jeremy; Owen, Benjamin; Pickford, Helena D.; Smith, Russell C. [Journal of the American Chemical Society, 2021, vol. 143, # 26, p. 9729 - 9736]
[4]Minakata, Satoshi; Kano, Daisuke; Oderaotoshi, Yoji; Komatsu, Mitsuo [Angewandte Chemie - International Edition, 2004, vol. 43, # 1, p. 79 - 81]
[5]Location in patent: scheme or table Sureshkumar, Devarajulu; Koutha, Srinivasamurthy; Ganesh, Venkataraman; Chandrasekaran, Srinivasan [Journal of Organic Chemistry, 2010, vol. 75, # 16, p. 5533 - 5541]

34
[ 928-95-0 ]
[ 108-24-7 ]
[ 2497-18-9 ]
[ 56922-75-9 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1999,p. 979 - 993

35
[ 928-95-0 ]
3-Furan-2-yl-4-vinyl-heptanoic acid (E)-hex-2-enyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With (E)-PrCH=CHCH₂ONa at 20℃; for 0.25h;

Reference： [1]Barluenga, Jose; Rubio, Eduardo; Lopez-Pelegrin, Jose A.; Tomas, Miguel [Angewandte Chemie - International Edition, 1999, vol. 38, # 8, p. 1091 - 1093]

36
[ 928-95-0 ]
[ 134902-40-2 ]
(+/-)-methyl (2R,3S)-2-[(2E)-2-hexenyloxy]-3-iodo-1-piperidinecarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	Stage #1: (+/-)-[(N-methoxycarbonyl)piperidine]-2-carboxylic acid With [bis(acetoxy)iodo]benzene; iodine In dichloromethane at 20℃; for 3h; Stage #2: (E)-2-Hexen-1-ol In dichloromethane at 20℃; for 1.5h; Further stages.;

Reference： [1]Boto; Hernandez; De Leon; Suarez [Journal of Organic Chemistry, 2001, vol. 66, # 23, p. 7796 - 7803]

37
[ 75-11-6 ]
[ 928-95-0 ]
trans-2-(propyl)cyclopropylmethanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: diiodomethane With diethylzinc In dichloromethane at 0℃; for 0.25h; Stage #2: (E)-2-Hexen-1-ol In dichloromethane at -20℃; for 0.25h; Stage #3: With titanium tetrachloride In dichloromethane at -20℃; for 7h; Further stages.;
23%	With lanthanum; iodine In tetrahydrofuran for 5h;

Reference： [1]Charette; Molinaro; Brochu [Journal of the American Chemical Society, 2001, vol. 123, # 49, p. 12160 - 12167]
[2]Nishiyama, Yutaka; Tanimizu, Hana; Tomita, Tsuyoshi [Tetrahedron Letters, 2007, vol. 48, # 36, p. 6405 - 6407]

38
[ 928-95-0 ]
[ 505-57-7 ]

Yield	Reaction Conditions	Operation in experiment
	With [{nBu₄N}5{PV₂Mo₁₀O₄₀}]; dinitrogen monoxide In benzonitrile at 150℃; for 15h;
	With 2,2,6,6-tetramethyl-piperidine-N-oxyl; H₅PV₂Mo₁₀O₄₀; oxygen In acetone at 100℃; for 10h;

Reference： [1]Ben-Daniel, Revital; Neumann, Ronny [Angewandte Chemie - International Edition, 2003, vol. 42, # 1, p. 92 - 95]
[2]Ben-Daniel; Alsters; Neumann [Journal of Organic Chemistry, 2001, vol. 66, # 25, p. 8650 - 8653]

39
[ 75-77-4 ]
[ 928-95-0 ]
[ 265135-87-3 ]

Yield	Reaction Conditions	Operation in experiment
98%	Stage #1: chloro-trimethyl-silane; (E)-2-Hexen-1-ol With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; Stage #2: With tert.-butyl lithium In tetrahydrofuran; hexane; pentane at -78 - -30℃;
68%	Stage #1: (E)-2-Hexen-1-ol With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: chloro-trimethyl-silane In tetrahydrofuran at -78℃; for 2.5h; Stage #3: With sec.-butyllithium In tetrahydrofuran at -78℃; for 2h;
57%	Stage #1: (E)-2-Hexen-1-ol With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane for 2.5h; Inert atmosphere; Stage #3: With sec.-butyllithium In tetrahydrofuran; hexane; cyclohexane for 2h; Inert atmosphere;

Reference： [1]Huckins, John R.; Rychnovsky, Scott D. [Journal of Organic Chemistry, 2003, vol. 68, # 26, p. 10135 - 10145]
[2]Kamimura, Akio; Kaneko, Yukio; Ohta, Ayaki; Matsuura, Kenji; Fujimoto, Yasuo; Kakehi, Akikazu; Kanemasa, Shuji [Tetrahedron, 2002, vol. 58, # 47, p. 9613 - 9620]
[3]Location in patent: experimental part An, Ilhwan; Onyeozili, Edith N.; Maleczka Jr., Robert E. [Tetrahedron Asymmetry, 2010, vol. 21, # 5, p. 527 - 534]

40
[ 928-95-0 ]
[ 141-97-9 ]
ethyl 2-acetyl-4-octenoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With pyridine; magnesium sulfate at 50℃; for 10h;

Reference： [1]Ozawa, Fumiyuki; Okamoto, Hideyuki; Kawagishi, Seiji; Yamamoto, Shogo; Minami, Tatsuya; Yoshifuji, Masaaki [Journal of the American Chemical Society, 2002, vol. 124, # 37, p. 10968 - 10969]

41
[ 67-56-1 ]
[ 928-95-0 ]
[ 305-53-3 ]
[ 256394-12-4 ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: (E)-2-Hexen-1-ol; monosodium iodoacetate With n-butyllithium In tetrahydrofuran at -78 - 20℃; Stage #2: methanol With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 0.5h;

Reference： [1]Helmboldt, Hannes; Hiersemann, Martin [Tetrahedron, 2003, vol. 59, # 23, p. 4031 - 4038]

42
[ 928-95-0 ]
4-iodo-5-methyl-oct-4-ene [ No CAS ]
5-Methyl-5-propyl-6-vinyl-nonan-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With copper(l) iodide; 3,4,7,8-Tetramethyl-o-phenanthrolin; caesium carbonate In xylene at 120℃; for 48h;

Reference： [1]Nordmann, Gero; Buchwald, Stephen L. [Journal of the American Chemical Society, 2003, vol. 125, # 17, p. 4978 - 4979]

43
[ 1123-28-0 ]
[ 928-95-0 ]
(2'E)-hexenyl 1-hydroxycyclohexanecarboxylate [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2003,p. 3637 - 3647

44
[ 928-95-0 ]
[ 75999-66-5 ]
(E)-2-hexenyl-N-(4-methoxyphenyl)trifluoroacetimidate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium hydride In tetrahydrofuran at 20℃; for 18h;
88%	With sodium hydride In tetrahydrofuran at 0 - 20℃;

Reference： [1]Overman, Larry E; Owen, Carolyn E; Pavan, Mary M; Richards, Christopher J [Organic letters, 2003, vol. 5, # 11, p. 1809 - 1812]
[2]Anderson, Carolyn E.; Donde, Yariv; Douglas, Christopher J.; Overman, Larry E. [Journal of Organic Chemistry, 2005, vol. 70, # 2, p. 648 - 657]

45
[ 928-95-0 ]
[ 111003-36-2 ]
[ 94992-76-4 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (E)-2-Hexen-1-ol With titanium(IV) isopropylate; tert.-butylhydroperoxide; bis(poly(ethylene glycol) monomethyl ether) L-tartrate ester In 2,2,4-trimethylpentane; dichloromethane at -20℃; for 12h; Stage #2: With L-Tartaric acid; iron(II) sulfate In 2,2,4-trimethylpentane; dichloromethane; water at 0℃; for 1h; Title compound not separated from byproducts;
84 % ee	With tert.-butylhydroperoxide In decane; dichloromethane at 54.84℃; enantioselective reaction;	2.3 Catalytic tests General procedure: The complexes and materials were tested in the epoxidation of olefins and allylic alcohols, such as cis-cyclooctene, styrene, 1-octene, trans-hex-2-en-1-ol, and R-(+)-limonene, using t-butylhydroperoxide (tbhp) as oxidant (Aldrich, 5.5M in n-decane). The catalytic oxidation tests were carried out at 328K under air in a reaction vessel equipped with a magnetic stirrer and a condenser. In a typical experiment, the vessel was loaded with olefin or alcohol (100mol%), internal standard (dibutyl ether, dbe), catalyst (1mol%), oxidant (200mol%), and 3mL of dichloromethane as solvent. The final volume of the reaction is ca. 6mL. Addition of the oxidant determines the initial time of the reaction. Conversion, product yields and stereochemistry were monitored by sampling periodically and analyzing them using a Shimadzu QP2100-Plus GC/MS system and a capillary column (Teknokroma TRB-5MS/TRB-1MS or Restek Rt-βDEXsm) operating in the linear velocity mode. All reactions were conducted under normal atmosphere. R-(+)-limonene epoxidation was carried out at different temperatures, 328K, 353K, and 393K, using dichloromethane, ethanol, and toluene as solvents, respectively.

Reference： [1]Reed, Neal N.; Dickerson, Tobin J.; Boldt, Grant E.; Janda, Kim D. [Journal of Organic Chemistry, 2005, vol. 70, # 5, p. 1728 - 1731]
[2]Fernandes, Cristina I.; Saraiva, Marta S.; Nunes, Teresa G.; Vaz, Pedro D.; Nunes, Carla D. [Journal of Catalysis, 2014, vol. 309, p. 21 - 32]

46
[ 928-95-0 ]
[ 64-19-7 ]
[ 2497-18-9 ]

Reference： [1]Tetrahedron,2005,vol. 61,p. 2011 - 2015
[2]Chemistry - A European Journal,2016,vol. 22,p. 9130 - 9134

47
[ 589-57-1 ]
[ 928-95-0 ]
[ 622-79-7 ]
benzyl-(1-propyl-allyl)-phosphoramidic acid diethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	Stage #1: diethyl phosphorylchloridite; (E)-2-Hexen-1-ol With triethylamine In diethyl ether at 0℃; for 0.5h; Stage #2: benzyl azide In xylene for 4h; Heating;