Catalytic Enantioselective Synthesis of Tetrahydroisoquinolines and Their Analogues Bearing a C4 Stereocenter: Formal Synthesis of (+)-(8S,13R)-Cyclocelabenzine

被引：56

作者：

Chen, Zhilong ^{[1
]}

Wang, Zhaobin ^{[1
]}

Sun, Jianwei ^{[1
]}

机构：

[1] Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Hong Kong, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2013年 / 19卷 / 26期

关键词：

alkaloids; asymmetric catalysis; nucleophilic addition; organocatalysis; strained molecules; CHIRAL BRONSTED ACIDS; ASYMMETRIC-SYNTHESIS; TRANSFER HYDROGENATION; OXETANES; OXIRANE; ROUTE;

D O I：

10.1002/chem.201301065

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A one-pot wonder: 1,2,3,4-Tetrahydroisoquinolines with a C4 stereocenter can be formed by using a one-pot multicomponent chiral phosphoric acid catalyzed transformation of a mixture of oxetane-tethered benzaldehydes, amines, and the dimethyl ester derivative of the Hantzsch ester (see scheme). This transformation can be used to prepare the spermidine alkaloid (+)-(8S,13R)-cyclocelabenzine. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：8426 / 8430

页数：5

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