反应详情

Add tetrabutylammonium fluoride (2.0 mL of 1.0 M solution in THF) to an ice-cold solution of 1-phenyl-2-nitroethane (0.51 mL, 3.79 mmol) in THF (2 mL). Stir 5 min and add 4-(S)-fluoro-2-(R)-formylpyrrolidine-1-carboxylic acid tert-butyl ester (0.58 g, 1.95 mmol) in THF (6 mL). Stir 90 min, dilute with ethyl acetate, wash with water (3×50 mL), saturated aqueous sodium chloride, dry (magnesium sulfate) and purify (silica gel chromatography, eluting with hexanes and ethyl acetate) to give the title compounds as foams, 4-(S)-fluoro-2-(R)-(1-(S)-hydroxy-2-(S)-nitro-3-phenylpropyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.21 g, 29%) and 4-(S)-fluoro-2-(R)-(1-(R)-hydroxy-2-(S)-nitro-3-phenylpropyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.33 g, 46%).

1. stirringStir 90 min
2. washwash with water (3×50 mL), saturated aqueous sodium chloride
3. dry with materialdry (magnesium sulfate)
4. custompurify
5. wash(silica gel chromatography, eluting with hexanes and ethyl acetate)