期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 134, 期 49, 页码 20049-20052出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja311150n
关键词
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资金
- Japan Society for the Promotion of Science (JSPS)
- Global COE Program (Chemistry Innovation through Cooperation of Science and Engineering)
- University of Tokyo
- MEXT (Japan)
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.
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