Highly Selective Catalyst-Directed Pathways to Dihydropyrroles from Vinyldiazoacetates and Imines

Abstract

Copper-catalyzed reactions of vinyldiazoacetates with imines occur via a pathway in which the activated imine undergoes electrophilic addition to the vinyldiazo compound, whereas reactions catalyzed by rhodium(II) proceed through a metal carbene to an intermediate iminiumylide. Both pathways exhibit high stereoselectivities.