Simple diastereoselectivity on addition of alpha-haloalkyl Grignard reagents to benzaldehyde

J Org Chem. 2003 May 30;68(11):4546-8. doi: 10.1021/jo034138m.

Abstract

The addition of alpha-haloalkyl Grignard reagents to benzaldehyde occurs with simple diastereoselectivity substantially higher than that of the corresponding lithium reagents. Reaction in the presence of dimethyl-aluminum chloride suppresses subsequent Oppenauer oxidation of the resulting Mg-alkoxides by excess benzaldehyde.