Asymmetric synthesis. Part II. The reduction of ketones with the lithium aluminium hydride–3-O-benzyl-1,2-O-cyclohexylidene-α-D-glucofuranose complex

Abstract

Asymmetric reduction of ketones with the lithium aluminium hydride–3-O-benzyl-1,2-cyclohexylidene-α-D-glucofuranose complex yields optically active alcohols of up to 40% optical purity. Using standardised filtered solutions of lithium aluminium hydride we obtained maximum selectivities with a 1:1 lithium aluminium hydride–sugar complex. All the alcohols thus obtained have the S-configuration and this constitutes a new and simple method for the determination of the absolute configuration of secondary alcohols.