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

Tetrahydroisoquinoline alkaloids with a C1 stereo- genic 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 enantiose- lective synthesis of chiral tetrahydroisoquinoline-alkaloid derivatives from readily available unsubstituted tetrahydroiso- quinolines, 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. 1I