Group 11 Metal Amide-Catalyzed Asymmetric Cycloaddition Reactions of Azomethine Imines with Terminal Alkynes

被引：117

作者：

Imaizumi, Takaki ^{[1
]}

Yamashita, Yasuhiro ^{[1
]}

Kobayashi, Shu ^{[1
]}

机构：

[1] Univ Tokyo, Sch Sci, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 49期

基金：

日本学术振兴会;

关键词：

ENANTIOSELECTIVE 3+2 CYCLOADDITION; 1,3-DIPOLAR CYCLOADDITION; ALDOL REACTION; BICYCLIC PYRAZOLIDINONES; ALDEHYDES; SARAIN;

D O I：

10.1021/ja311150n

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We developed a 1,3-dipolar cycloaddition reaction of azomethine imines with terminal alkynes catalyzed by group 11 metal amides to provide N,N-bicyclic pyrazolidinone derivatives. This reaction afforded the cycloadducts in a unique 5,7-disubstituted manner. Furthermore, we succeeded in applying this catalysis to asymmetric reactions, and the desired heterocycles were produced in high yields with exclusive regioselectivity and high enantioselectivity. Mechanistic studies elucidated a stepwise reaction pathway and critical features that determine the regioselectivity.

引用

页码：20049 / 20052

页数：4

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