Preparation of chiral 1-phenylethanols and bromides

Abstract

A fast, convenient procedure for preparing and resolving moderate to large quantities of chiral secondary alcohols is described. The general procedure involves a one-pot conversion of the ketone (various acetophenones) to the half-ester of a diacid (succinic, phthalic… ) and resolution with (+)- and (−)-1-phenylethylamines. Overall yields of the enantiomeric alcohols, the variously substituted 1-phenylethanols, are generally 65–85% with optical purities of approximately 90%. Properties and optical rotations of a number of chiral 1-phenylethanols and of the bromides made from them are tabulated. A discussion of optical purity determinations using nmr methods is included and absolute configurations are reported.