Optical Resolution of 2-Amino-1,2-diphenylethanol by Preferential Crystallization and Its Utilization in Fractional Crystallization and Enantioselective Reduction of Prochiral Ketones

Article abstract of DOI:10.1246/bcsj.55.1568

(-/+)-erythro-2-Amino-1,2-diphenylethanol prepared from benzoin oxime by catalytic reduction was successfully resolved into pair of optically active forms by preferential crystallization.The optically active amino alcohol was found to be useful as a basic resolving agent for optical resolution of tartaric acid, trans-2,3-oxiranedicarboxylic acid, 2-hydroxy-2-phenylpropionic acid, and 3-endo-benzamido-5-norbornene-2-endo-carboxylic acid.Chiral hydrides prepared from lithium aluminium hydride and optical active threo- and erythro-2-amino-1,2-diphenylethanol derivatives were applied to the enantioface differentiating reduction of prochiral ketones to give the corresponding optically active alcohols in the 26-72percent optical purities.