Enantioselective Double Manipulation of Tetrahydroisoquinolines with Terminal Alkynes and Aldehydes under Copper(I) Catalysis |
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| Authors: | Weilong Lin Prof. Dr. Shengming Ma |
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| Affiliation: | 1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (P.R. China);2. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 North Zhongshan Lu, Shanghai 200062 (P.R. China) |
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| 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 CuI‐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. |
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| Keywords: | alkynylation asymmetric catalysis chirality copper tetrahydroisoquinoline alkaloids |
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