Alkyl metal asymmetric reduction. Part VIII. Stereoselectivity of the reduction of alkyl phenyl ketones by optically active aliphatic Grignard reagents

Abstract

The reactions between alkyl phenyl ketones and optically active aliphatic Grignard reagents, containing groups of different steric requirements on the chiral carbon atom, have been investigated. Both reduction and addition products were formed, their relative amounts being dependent on the structure of both the ketone and the Grignard reagent. In all cases, optically active carbinols were recovered, whatever the distance of the asymmetric carbon atom from the magnesium atom. The factors controlling the course of the reaction and its stereoselectivity are discussed.