反应详情

(2R)-2-benzhydryl-oxirane (0.5 g, 2.38 mmol) 23a was dissolved in dry THF (5 ml) and was added into a dry THF solution at −78° C. containing CuI (0.045 g, 0.24 mmol) and vinylmagnesium bromide (5.95 ml of 1.0M solution in THF, 5.95 mmol). The reaction mixture was stirred and allowed to reach room temperature over a period of 2 h, and then quenched with saturated NH4Cl solution. The aqueous phase was extracted with ethyl acetate (3×30 ml). The combined organic phase was washed with brine and dried over anhydrous Na2SO4. The solvent was removed and the residue was purified by flash chromatography on silica gel (Hexane/Ethyl Ether=4:1) to give 0.4 g (2S)-1,1-diphenyl-pent-4-ene-2-ol (70%, [α]D=(−)25, c=1, MeOH).

1. customquenched with saturated NH4Cl solution
2. extractionThe aqueous phase was extracted with ethyl acetate (3×30 ml)
3. washThe combined organic phase was washed with brine
4. dry with materialdried over anhydrous Na2SO4
5. customThe solvent was removed
6. customthe residue was purified by flash chromatography on silica gel (Hexane/Ethyl Ether=4:1)