A paradigm for diastereoselectivity in electrophilic attack on trigonal carbon adjacent to a chiral centre: the methylation and protonation of some open–chain enolates

Abstract

Methylation of the enolates (3), and protonation of the enolates (4), are diastereoselective in conformity with a recently formulated rule, and are, with one exception, selective in the opposite sense to nucleophilic attack on the corresponding aldehydes (7) and ketones (8).