Stereoselective Synthesis of Highly Substituted α-Silylamines from Silylmethyl Azides under Ru Catalysis

Abstract

A synthetic strategy towards highly substituted -silyl homoallylic amines was discovered. The key event is the unique synthesis of N-unsubstituted -silylimines from azide precursors under mild conditions. Of particular note is the unprecedented access to -silylamines possessing multiple stereocenters and functional groups with high diastereo- and enantioselectivity. The synthetic utility of the method was demonstrated by the use of the silyl moiety as the key element that enables late-stage modification for the iminium ion mediated oxidative cyclization.