N-Heterocyclic Carbene-Catalyzed [3+4] Cycloaddition and Kinetic Resolution of Azomethine Imines

被引：229

作者：

Wang, Ming ^{[1
]}

Huang, Zhijian ^{[1
]}

Xu, Jianfeng ^{[1
]}

Chi, Yonggui Robin ^{[1
]}

机构：

[1] Nanyang Technol Univ, Div Chem & Biol Chem, Sch Phys & Math Sci, Singapore 637371, Singapore

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2014年 / 136卷 / 04期

基金：

新加坡国家研究基金会;

关键词：

ENANTIOSELECTIVE 1,3-DIPOLAR CYCLOADDITION; PYRAZOLIDINONE DERIVATIVES; SECONDARY ALCOHOLS; TERMINAL ALKYNES; ENALS; ALDEHYDES; YLIDES; BASE; ANNULATIONS; ACYLATION;

D O I：

10.1021/ja411110f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first N-heterocyclic carbene (NHC)-catalyzed [3+4] cycloaddition of azomethine imines and enals is disclosed. Oxidative catalytic remote activation of enals affords 1,4-dipolarophile intermediates that react with 1,3-dipolar azomethine imines to generate dinitrogenfused seven-membered heterocyclic products with high optical purities. Our approach also provides effective kinetic resolution of azomethine imines, in which the substrate chiral center that is remote from the NHC catalyst can be well resolved.

引用

页码：1214 / 1217

页数：4

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