Enzyme‐Catalyzed Kinetic Resolution of 1,3‐anti‐Diol Monoesters — Efficient Preparation of Enantiomerically Highly Enriched and Unsymmetrically Substituted 1,3‐anti‐Diols.

Abstract

Biochemical syntheses O 0035Enzyme-Catalyzed Kinetic Resolution of 1,3-anti-Diol Monoesters -Efficient Preparation of Enantiomerically Highly Enriched and Unsymmetrically Substituted 1,3-anti-Diols. -Esterification of title anti-diol monoesters (I) with vinyl acetate is smoothly catalyzed by immobilized Candida antarctica lipase B (Novozym 435) to furnish the mixed esters (III) as well as enantioenriched monoesters (I) in yields of about 50% and optical purity of 91 -99% e.e. Alkaline hydrolysis then provides the enantioenriched diols. Alternatively, the Novozym-catalyzed esterification of racemic diols (IV) with vinyl acetate proceeds efficiently to give enantioenriched monoesters (V) as well as enantiopure diols (IV). -(JAKOB, F.; SCHNEIDER*, C.; Eur.