Asymmetric syntheses. Part 11. Reduction of ketones and related ketone oximes with lithium aluminium hydride–3-O-cyclohexylmethyl-1,2-O-cyclohexylidene-α-D-glucofuranose complex to give optically active alcohols and amines

Abstract

The asymmetric reduction of ketones and structurally related isoelectronic ketone oximes with lithium aluminium hydride–3-O-cyclohexylmethyl-1,2-O-cyclohexylidene-α-D-glucofuranose complex yields optically active alcohols of up to 42% optical purity and optically active amines of up to 52% optical purity, respectively. The resulting alcohols as well as amines all have the S-configuration. When the asymmetric reduction is carried out with the ethanol-modified glucofuranose complex, the resulting alcohols and amines have the R-configuration.