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

被引：134

作者：

Lin, Weilong ^{[1
]}

Cao, Tao ^{[1
]}

Fan, Wu ^{[2
]}

Han, Yulin ^{[1
]}

Kuang, Jinqiang ^{[1
]}

Luo, Hongwen ^{[2
]}

Miao, Bukeyan ^{[2
]}

Tang, Xinjun ^{[1
]}

Yu, Qiong ^{[2
]}

Yuan, Weiming ^{[2
]}

Zhang, Jiasheng ^{[1
]}

Zhu, Can ^{[1
]}

Ma, Shengming ^{[1
,2
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

[2] E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 01期

基金：

中国国家自然科学基金;

关键词：

alkynylation; asymmetric catalysis; chirality; copper; tetrahydroisoquinoline alkaloids; SP(3) C-H; ASYMMETRIC TRANSFER HYDROGENATION; TERTIARY-AMINES; RECENT PROGRESS; BONDS ADJACENT; ISOQUINOLINE ALKALOIDS; HIGHLY EFFICIENT; ALKYNYLATION; NITROGEN; ACCESS;

D O I：

10.1002/anie.201308699

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：277 / 281

页数：5

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