Phosphine-catalyzed sequential [4+ ]/[2+3] annulation of o-amino arylaldimines with Morita–Baylis–Hillman (MBH) carbonates

Abstract

Herein, we report an efficient phosphine-catalyzed sequential [4+1]/[2+3] annulation reaction of o-amino arylaldimines with Morita–Baylis–Hillman (MBH) carbonates. A wide range of hexahydropyrrolo[3,2-b]indoles bearing three consecutive stereogenic centers were obtained in satisfactory yields with excellent diastereoselectivity (all >20:1 d.r.). This transformation is notable for simultaneously forming one C–C bond, two C–N bonds, and two five-membered N-heterocyclic rings in one-pot, thereby offering high bond-forming efficiency.