Combining proline and 'click chemistry': a class of versatile organocatalysts for the highly diastereo- and enantioselective Michael addition in water

被引：99

作者：

Yan, Ze-Yi

Niu, Yan-Ning

Wei, Hal-Long

Wu, Lu-Yong

Zhao, Ya-Bin

Liang, Yong-Min ^{[1
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

[2] Chinese Acad Sci, Lanzhou Inst Chem Phys, Lanzhou 730000, Peoples R China

来源：

TETRAHEDRON-ASYMMETRY | 2006年 / 17卷 / 23期

基金：

中国国家自然科学基金;

关键词：

D O I：

10.1016/j.tetasy.2006.12.003

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Based on 'click chemistry' conditions, a class of novel, facile, versatile pyrrolidine-based triazole derivatives were prepared, and proved to be efficient catalysts for the highly diastereoselective and enantioselective Michael addition of ketones to nitroalkenes. The Cu(I)-catalyzed 1,3-dipolar 'click' azide-alkyne cycloaddition provides modular and tunable features for the pyrrolidine-based triazole organocatalysts, and the resulting triazole moiety can serve as a phase tag to complete the reaction in water with an excellent yield and high enantiomeric excess. (c) 2007 Elsevier Ltd. All rights reserved.

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收藏

页码：3288 / 3293

页数：6

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