Organocatalytic and stereoselective [3+2] cycloadditions of azomethine imines with α,β-unsaturated aldehydes

被引：153

作者：

Chen, Wei

Yuan, Xiang-Hong

Li, Rui

Du, Wei

Wu, Yong

Ding, Li-Sheng

Chen, Ying-Chun ^{[1
]}

机构：

[1] Sichuan Univ, W China Sch Pharm, Key Lab Drug Targeting Educ Minist, Chengdu 610041, Peoples R China

[2] Sichuan Univ, W China Sch Pharm, Dept Med Chem, Chengdu 610041, Peoples R China

[3] Chinese Acad Sci, Chengdu Inst Biol, Chengdu 610041, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2006年 / 348卷 / 14期

关键词：

azomethine imines; bipyrazolidin-3-one; diarylprolinols; dipolar cycloaddition; organocatalysis; unsaturated aldehydes;

D O I：

10.1002/adsc.200606102

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Bipyrazolidin-3-one derivatives are biologically significant compounds and their importance has increased in the past decades. In this paper, the first stereoselective [3 + 2] dipolar cycloadditions of azomethine imines with alpha,beta-unsaturated aldehydes catalyzed by readily available alpha,alpha-diarylprolinol salts are reported, providing a facile route to the synthesis of various chiral bipyrazolidin-3-one derivatives under mild conditions. The organocatalyst 1g with strongly electron-withdrawing groups exhibited the best stereoselectivity (exo:endo up to 98:2, for exo product up to 97% ee), in the combination with trifluoroacetic acid.

引用

页码：1818 / 1822

页数：5

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