Asymmetric Catalysis with “Planar-Chiral” Derivatives of 4-(Dimethylamino)pyridine

Whereas chiral Lewis acid catalysis has been intensively investigated, chiral Lewis base (nucleophilic) catalysis has been comparatively neglected. We have developed "planar-chiral" derivatives of 4-(dimethylamino)pyridine (DMAP), a highly versatile nucleophilic catalyst, that are effective in a diverse array of processes, including the Staudinger synthesis of beta-lactams, the acylation of silyl ketene acetals, and the kinetic resolution of amines.