Water → (1S,2S)-1-(3,4,5-trifluorophenyl)propane-1,2-diol

Participants

Reaction Conditions

Reaction Steps

1,2,3-Trifluoro-5-[(E)-propenyl]-benzene (5.83 g) was added to an ice-cooled mixed solution of AD-Mix-α (47.5 g) and methanesulfonamide (3.22 g) in tert-butanol (170 ml) and water (170 ml), and the reaction solution was stirred at 5° C. overnight. Then, sodium sulfite (51 g) was added to the reaction solution, which was then stirred for one hour. The reaction solution was subjected to extraction with methylene chloride three times. The combined organic layers were washed with a 2 N sodium hydroxide solution, and then the sodium hydroxide layer was subjected to extraction with methylene chloride again. The organic layers were combined and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 1:1) to obtain 5.54 g of the title compound.

Provenance & Evidence