Enzymatic Synthesis of (-)- and (+)-Acetoxyhexamides and (-)- and (+)-Hydroxyhexamides

Abstract

The enantioselective hydrolysis of (±)-4-(1-acetoxyethyl)-N-(cyclohexylcarbamoyl)-benzenesulfonamides 3 with lipase Amano P from Pseudomonas sp. in a water-saturated solvent gave (R)-4-(1-hydroxyethyl)-N-(cyclohyxylcarbamoyl)benzenesulfonamide 2 (39%, >99% ee) and unchanged (S)-3 (50%, 62% ee). On the other hand, enantioselective esterification of (±)-2 with lipase Amino P in the presence of vinyl acetate provided (R)-3 (41%, >99% ee) and unchanged (S)-2 (46%, 78% ee).