Design and Evaluation of a Practical Camphor-Based Methyl Ketone Enolate for Highly Stereoselective “Acetate” Aldol Reactions

Abstract

A trajectory close to the chiral auxiliary must be followed by the electrophilic aldehyde on attacking the lithium enolate of II. Consequently, unprecedented diastereomeric excesses in the 95–98% range are obtained for the aldol reaction of II with a variety of aldehydes. This is the first methyl ketone-enolate strategy that allows recovery of the chiral controller of the process.