Enantioselective Double Manipulation of Tetrahydroisoquinolines with Terminal Alkynes and Aldehydes under Copper(I) Catalysis

Abstract

Abstract Tetrahydroisoquinoline alkaloids with a C1 stereogenic center are a common unit in many natural and non‐natural compounds of biological importance. Herein we describe a novel Cu I ‐catalyzed highly chemo‐ and enantioselective synthesis of chiral tetrahydroisoquinoline‐alkaloid derivatives from readily available unsubstituted tetrahydroisoquinolines, aldehydes, and terminal alkynes in the presence of the ligand ( R , R )‐N‐pinap. This synthetic operation installs two substituents in the 1‐ and 2‐positions.