1: 23%
2: 42% |
With ammonium hydroxide; titanium(III) chloride In methanol at 0 - 20℃; for 0.0833333h; |
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18.5% |
With potassium hydride In tetrahydrofuran for 0.0833333h; Yield given; |
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With isopropyl alcohol at 25℃; for 24h; other cyclic ketones, other catalysts, other reaction times, other temperatures; reactivity and stereoselectivity of neutral transition metal polyhydrides in the catalytic transfer hydrogenation; |
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at 25℃; for 1176h; Aspergillus repens MA0197; |
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With 9-fluorenyloxy-AlCl2 In diethyl ether for 0.25h; Ambient temperature; other reducing reagents; |
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With tert-butylmagnesium chloride; bis(2,6-di-tert-butyl-4-methylphenoxide)methylaluminum In diethyl ether; toluene by variation of the reaction conditions; |
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With chloro-trimethyl-silane; sodium hydride; zinc(II) chloride In tetrahydrofuran at 45℃; for 0.25h; other reducing agents, rection times, temperatures; |
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With tri-tert-butoxyaluminum hydride In tetrahydrofuran at 9.9℃; var. temp., ΔG(excit.), ΔH(excit.), ΔS(excit.); |
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With ZnCRASi (t-amylalcohol, NaH, ZnCl2, Me3SiCl) In tetrahydrofuran at 45℃; for 0.25h; other complex reducing agents; |
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With ethanol at 25℃; |
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In ethanol; water at 0 - 45℃; in Tris-HCl buffer at pH 8,5; studied: stereochemistry, effect of substituent chain length and branching; determined: k, EA, ΔH*, ΔS*, ΔG*; |
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With sodium tetrahydroborate In methanol; dichloromethane at -78℃; Competition with ..(aldehydes 1a, 1b, 1c, 1d).. and ..(enones 4a, 4b, 4c, 4d, 4e, 4f, 4g); |
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1: 15 % Chromat.
2: 85 % Chromat. |
With sodium tetrahydroborate; 1,2,4,5-tetramethylbenzene; oxygen In tetrahydrofuran |
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With isopropoxydiisobutylaluminum In diethyl ether at 25℃; for 3h; stereoselectivity; various periods of time (3-120 h); further ketones; |
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With 1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol In chloroform at 30℃; for 6h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
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With tert-butylmagnesium chloride; bis(2,6-di-tert-butyl-4-methylphenoxide)methylaluminum In diethyl ether; hexane; toluene at -23℃; for 4h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
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With chloro-trimethyl-silane; sodium alkoxide of 2,5 hexanediol; nickel diacetate In tetrahydrofuran at 63℃; for 18h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
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With hydrogen In ethanol at 25℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
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With sodium borohydride-mandelic acid In isopropyl alcohol for 2h; Heating; Yield given; |
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With polydibenzo-18-crown-6-borohydride In ethanol at 40 - 50℃; for 22h; Yield given. Yields of byproduct given; |
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With ZnCRASi (t-AmOH, NaH, ZnCl2, Me3SiCl) In tetrahydrofuran at 45℃; for 0.25h; other complex reducing agents; Yield given. Yields of byproduct given; |
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With methylaluminum bis(2,6-di-tert-butylphenoxide); tert-butylmagnesium chloride In diethyl ether; toluene at -23℃; for 4h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
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With lithium methyl trihydrido borate In diethyl ether at -78℃; for 2h; Yield given. Yields of byproduct given; |
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With sodium tetrahydroborate; copper(II) exchange resin In ethanol; water for 4.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
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With lithium dimethylamino borohydride In tetrahydrofuran at 0℃; for 1h; |
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With Li(n-Pr)2BH3 In tetrahydrofuran at 0℃; for 0.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
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With potassium hydroxide; tris(triphenylphosphine)ruthenium(II) chloride; hydrogen; ethylenediamine In isopropyl alcohol at 28℃; for 1h; Title compound not separated from byproducts; |
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With polymethylhydrosiloxane; tetrabutyl ammonium fluoride 1.) THF, -70 deg C, 30 min, 2.) THF, -70 deg C -> room temperature, 1 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; |
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With thexyl-s-butoxyborane In tetrahydrofuran at 25℃; for 168h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
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With sodium hydroxide; 1,1,5,5,5-hexamethyl-3-[(trimethylsilyl)oxy]trisiloxane; tetrabutyl ammonium fluoride 1.) THF, room t., 2.) THF; Yield given. Multistep reaction. Yields of byproduct given; |
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With diisobutylaluminium hydride In diethyl ether for 5h; Heating; Yield given. Yields of byproduct given; |
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With lithium aluminium tetrahydride; (+/-)-threo-1,16-dibenzyloxy-7,8-dihydroxyhexadecane In tetrahydrofuran Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
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With nickel at 125 - 130℃; Hydrogenation.Reinigung ueber das 4-Benzoyl-Derivat nach Abtrennung durch partielle Acetylierung mit 2-Nitro-benzoylchlorid in Pyridin; |
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With hydrogenchloride; acetic acid; platinum at 125 - 130℃; Hydrogenation; |
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With 1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol In chloroform at 30℃; for 1h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
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With chloro-trimethyl-silane; sodium hydride; cadmium(II) chloride In tetrahydrofuran at 63℃; for 3h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
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With LiBH3NC(CH3)2(CH2)3C(CH3)2 In tetrahydrofuran at 0℃; for 1h; |
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With sodium hydroxide; polymethylhydrosiloxane; N-benzyl-trimethylammonium hydroxide 1.) THF, room t., 2.) THF; Yield given. Multistep reaction; |
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With manganese(III) (Z)-2,2,6,6-tetramethyl-5-oxohept-3-en-3-olate; phenylsilane; oxygen In 1,2-dichloro-ethane; isopropyl alcohol at 23℃; Title compound not separated from byproducts; |
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With sodium hydroxide; 1,2-(4-H2O3PC6H4)2-N,N'-dimethylethane-1,2-diamine; hydrogen In methanol; water at 50℃; for 21h; |
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With SBA-15; Zr(OPr); isopropyl alcohol for 0.5h; Heating; |
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With hydrogenchloride; isopropyl alcohol for 0.266667h; Heating; Title compound not separated from byproducts.; |
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Stage #1: 1-methylcyclohexan-4-one With Al-trifluoromethanesulfonyldiisobutylalane In diethyl ether at 25℃; for 72h; Inert atmosphere;
Stage #2: With hydrogenchloride; water In diethyl ether optical yield given as %de; diastereoselective reaction; |
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70 % de |
With potassium hydroxide In isopropyl alcohol at 85℃; for 12h; |
Catalyst Testing
General procedure: In a typical reaction, substrate (10 mmol), Ru/Carbon (100 mg, 0.005 mmol of Ruthenium from ICP analysis), 0.01 g KOH and 100 mmol of 2-propanol were placed in a round bottom flask (batch reactor) fitted with reflux condenser, equipped with a magnetic stirrer and immersed in a thermostatic oil bath for maintaining the desired reaction temperature. The reactions was conducted at the desired temperature and the progress of the reaction was monitored by withdrawing reaction mixture samples periodically, centrifuged and analyzed for their compositions a Agilent gas chromatograph with a capillary column (cross-linked methyl silicone gum, HP1, 50 m × 0.2 mm i.d.) and a flame ionization detector (FID). The product identification was achieved by using standards and GCMS (Agilent). |
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With methanol; sodium tetrahydroborate at 0℃; for 1h; |
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