Preparation of chiral secondary alcohols via enantioselective hydrolysis of corresponding esters with a microorganism.

Abstract

Esters of secondary alcohols were enantioselectively hydrolyzed with ^{Brevibacterium ammoniagenes} IAM 1645, ATCC 6872 to give the corresponding chiral alcohols and esters. While the esters of alkyl vinyl carbinols gave (S)-alcohols, dialkyl carbinol esters were hydrolyzed to (R)-alcohols of rather low optical purities. Hydrolysis of α-phenethyl acetate proceeded smoothly resulting in the formation of (R)-α-phenethyl alcohol in good optical yield. The structure of the acyl moiety of 1-tridecen-3-yl esters seriously influenced the rate and optical yield of the reaction, and the acetate was found to give the best results.