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With (R)-2-(diphenylmethyl)pyrrolidine; sodium acetate In dichloromethane at 25℃; for 20h; stereoselective reaction;
Asymmetric Organocatalytic Doubly Cycloadditive Cascade Reaction; General Procedure
General procedure: In an ordinary 4 mL glass vial, equipped with a Teflon-coated magnetic stirring bar and a screw cap, the corresponding aldehyde 2 (0.22 mmol, 2.2 equiv.), 1,3,6-trimethyl-5-formyluracil (1; 18.2 mg, 0.10 mmol, 1 equiv.), and NaOAc (8.2 mg, 0.10 mmol, 1 equiv.) were dissolved in CH2Cl2 (0.4 mL) and the catalyst 4e (4.7 mg, 0.02 mmol, 0.2 equiv) was added and the mixture was stirred for 20 h at 25 °C. After this time, the mixture was diluted with CH2Cl2 (0.4 mL), cooled to 10 °C and the ylide 8 (100 mg, 0.3 mmol, 3 equiv.) was added and stirring was maintained at 10 °C for 20 h. Pure products 9 were isolated as single diastereoisomers by flash chromatography on silica gel (eluent: hexanes/EtOAc from 4:1 to 3:1).
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