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Enantioselective Double Manipulation of Tetrahydroisoquinolines with Terminal Alkynes and Aldehydes under Copper(I) Catalysis
Author(s) -
Lin Weilong,
Cao Tao,
Fan Wu,
Han Yulin,
Kuang Jinqiang,
Luo Hongwen,
Miao Bukeyan,
Tang Xinjun,
Yu Qiong,
Yuan Weiming,
Zhang Jiasheng,
Zhu Can,
Ma Shengming
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201308699
Subject(s) - stereocenter , enantioselective synthesis , tetrahydroisoquinoline , catalysis , chemistry , combinatorial chemistry , ligand (biochemistry) , copper , stereochemistry , organic chemistry , receptor , biochemistry
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.