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

Abstract

Fujimoto H., Nakayasu B., Tobisu M.. Synthesis of γ-Lactams from Acrylamides by Single-Carbon Atom Doping Annulation. Journal of the American Chemical Society 145, 19518 (2023); https://doi.org/10.1021/jacs.3c07052.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

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