Diastereoselective synthesis of tetrahydroquinolines via a palladium-catalyzed Heck-Suzuki cascade reaction

A method for the diastereoselective synthesis of tetrahydroquinolines via a palladium-catalyzed Suzuki terminated Heck reaction is described. The reaction provides access to tetrahydroquinolines containing both quaternary and tertiary stereocenters. Ligand effects, a rationale for the high level of diastereoselectivity, and a mechanistic hypothesis are discussed. (C) 2012 Elsevier Ltd. All rights reserved.