On the origins of diastereoselectivity in the alkylation of enolates derived from N-1-(1'-naphthyl)ethyl-O-tert-butylhydroxamates: chiral Weinreb amide equivalents

A chiral relay mechanism is utilized to rationalize the stereochemical outcome observed upon alkylation of enolates derived from N-1-(1'-naphthyl)ethyl-O-tert-butylhydroxamates (chiral Weinreb amide equivalents). The conformation of the O-tert-butyl group and the configuration adopted by the adjacent pyramidal nitrogen atom is found to be dictated by the configuration of the N-1-(1'-naphthyl)ethyl group.