(S)-(-)-Glycidol

Typical procedure: To a cooled solution (0 °C) of (S)-glycidol (5.0 g) and imidazole (5.97 g) in CH2Cl2 (250 mL) under N2 was added TBDPSCl (18.55 g) diluted in CH2Cl2 (20 mL). The solution was allowed to warm to room temperature and stirred for 1.5 h. The white slurry was quenched by the addition of water. The organic layer washed with brine, dried over Na2SO4, and concentrated to give TBDPS-(S)-glycidol (21.1g, quant.) of colorless oil which was used directly at the next step. The TBDPS-(S)-glycidol and CuI (1.29 g) in THF (40 mL) under N2 was added dropwise vinylmagnesium bromide (338 mL, 1 M in THF) at -25 °C. After stirring 1 h at -25 °C, the reaction was quenched with sat. NH4Cl solution (400 mL). After warming to room temperature, 5 % aqueous H2SO4 was added to dissolve the salts and the mixture was extracted with Et2O (400 mL). The organic layer was washed with sat. NaHCO3 and brine, dried over Na2SO4. The solution was decanted and concentrated. The residue was purified by column chromatography to give the desired alcohol as a colorless oil (19.3g, 84 %).