Stannylcupration as a Highly Regio- and Stereoselective route to 2-Substituted Tributylstannyl Allylamines

Abstract

N-Protected propargylamines react with Bu₃Sn(Bu)Cu(CN)Li₂, under very mild conditions, affording, in high regiospecific fashion after quench with electrophiles, the corresponding 2-substituted 3-(tributylstannyl)allylamines, in good to excellent yields. These, upon transmetalation and further reaction with electrophiles, give stereodefined 1,2-disubstituted allylamines.