Asymmetric Inverse-Electron-Demand 1,3-Dipolar Cycloaddition of C,N-Cyclic Azomethine Imines: An Umpolung Strategy

被引：133

作者：

Hashimoto, Takuya ^{[1
]}

Omote, Masato ^{[1
]}

Maruoka, Keiji ^{[1
]}

机构：

[1] Kyoto Univ, Dept Chem, Grad Sch Sci, Sakyo Ku, Kyoto 6068502, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 15期

关键词：

Bronsted acids; carboxylic acid; cycloadditions; organocatalysis; umpolung; CHIRAL DICARBOXYLIC-ACID; N-BOC IMINES; LEWIS-ACID; ENANTIOSELECTIVE ADDITION; TERMINAL ALKYNES; NITRONES; N; N-DIALKYLHYDRAZONES; N-DIMETHYLHYDRAZONES; CONSTRUCTION; ALDEHYDES;

D O I：

10.1002/anie.201100331

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Oompa loompa: The title reaction has been accomplished with high stereoselectivity by use of an axially chiral dicarboxylic acid (see scheme). Employment of vinylogous aza-enamines as novel dipolarophiles was also implemented to establish a new concept of the inverse-electron-demand umpolung 1,3-dipolar cycloaddition. Bz=benzoyl, EDG=electron-donating group. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：3489 / 3492

页数：4

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