Asymmetric cycloaddition of anthrone and maleimides catalyzed by C2-chiral pyrrolidines

被引：46

作者：

Uemae, K ^{[1
]}

Masuda, S ^{[1
]}

Yamamoto, Y ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Human & Environm Studies, Sakyo Ku, Kyoto 6068501, Japan

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2001年 / 09期

关键词：

D O I：

10.1039/b100961n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Catalytic asymmetric cycloaddition of anthrone dagger with N-alkyl- and N-arylmaleimides with various substituents in the aromatic ring was carried out in the presence of C-2-chiral pyrrolidines to afford chiral, non-racemic [4+2] adducts. Among them, good catalytic activity was observed with the pyrrolidines with a N-(4-pyridyl)methyl group 1h, which was discussed from the viewpoint of conformational analysis. The best stereoselectivity of 87% ee was attained when the reaction of N-(2-tert-butylphenyl)maleimide 4j and anthrone was promoted with 1h.

引用

页码：1002 / 1006

页数：5

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