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 a solution mixture of tert-butanol (170 mL) and water (170 mL) of AD-Mix-α (47.5 g) and methanesulfonamide (3.22 g) under ice-cooling. This reaction solution was stirred at 5° C. overnight. Then, sodium sulfite (51 g) was added to the reaction solution, and the resulting mixture was stirred at room temperature for 1 hr. The reaction solution was extracted with methylene chloride three times. All 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. All the organic layers were combined, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue 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