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

Participants

Reaction Conditions

Reaction Steps

To an ice-cooled solution mixture of tert-butanol (170 mL) and water (170 mL) of AD-Mix-α (47.5 g) and methanesulfonamide (3.22 g), 1,2,3-trifluoro-5-((E)-propenyl)benzene (5.83 g) was added. The resulting reaction solution was stirred at 5° C. overnight, and then sodium sulfite (51 g) was added thereto. The resulting reaction solution was stirred at room temperature for 1 hr, and then extracted with methylene chloride three times. The organic layers were combined and washed with a 2 N sodium hydroxide aqueous solution. The sodium hydroxide layer was re-extracted with methylene chloride. The organic layers were combined, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 1:1) to give 5.54 g of the title compound. The physical property values of this compound were as follows:

Provenance & Evidence