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
收藏
页码：20049 / 20052
页数：4
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