Palladium-catalyzed cyclocarbonylation of unsaturated amines. Chemo- and stereoselective synthesis of N-heteroaryl γ- and δ-lactams

Abstract

Palladium-catalyzed cyclocarbonylation of N-heteroaryl-N-homoallyl amines led to γ-and δ-lactams with good yields and in a stereo-and regioselective way. The regio-and stereoselectivity of the methodology was investigated by changing the heterocycle attached to the amine and varying the reaction solvent and the metal ligand. In order to explain the obtained results, a cyclocarbonylation mechanism with the participation of the heterocyclic moiety is suggested.