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
收藏
页码：3489 / 3492
页数：4
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