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.