Synthesis of γ-Lactams from Acrylamides by Single-Carbon Atom Doping Annulation.

Abstract

A protocol for single-carbon atom doping annulation is reported, which enables the conversion of acrylamides into homologated γ-lactams through the cleavage of two σ-bonds and the formation of four new σ-bonds at the single carbon center. The key strategy is the use of N-heterocyclic carbenes as an atomic carbon equivalent by acting as carbon atom donors through the loss of a 1,2-diimine moiety. Experimental and computational studies reveal that the reaction proceeds through a spirocyclic intermediate, followed by the disassembly of the N-heterocyclic carbene skeleton via proton transfer.