Practical and Highly Selective Oxazolidinethione-Based Asymmetric Acetate Aldol Reactions with Aliphatic Aldehydes

Abstract

The utility of a valine-derived oxazolidinethione for auxiliary-based asymmetric acetate aldol reactions is reported. Titanium(IV) chloride, along with (−)-sparteine and N-methylpyrrolidinone, is employed for enolization. Subsequent aldol reaction with aliphatic aldehydes occurs with high diastereoselectivity (from 92:8 to 99:1 dr).