Synthesis of functionalized tetrahydroisoquinolines via palladium-catalyzed 6-exo-dig carbocyclization of 2-bromo-N-propargylbenzylamines

An efficient twostep synthetic strategy for tetrahydroisoquinolines has been described. The first step involves Cul catalyzed three-component coupling reaction of terminal alkyne, aldehyde and amine that provides the requisite propargyl amine. Regio- and stereoselective palladium-catalyzed 6-exo-dig carbocyclization of propargyl amine, which provides a concise access to functionalized tetrahydroisoquinolines in good yields has been developed. (c) 2011 Elsevier Ltd. All rights reserved.