Phosphite-mediated annulation: an efficient protocol for the synthesis of multi-substituted cyclopropanes and aziridines

被引：11

作者：

Liu, Xu-Guang ^{[1
,2
]}

Wei, Yin ^{[3
]}

Shi, Min ^{[1
,2
,3
]}

机构：

[1] E China Univ Sci & Technol, Adv Mat Lab, Shanghai 200237, Peoples R China

[2] E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China

[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

TETRAHEDRON | 2010年 / 66卷 / 01期

基金：

中国国家自然科学基金;

关键词：

Phosphite; Phosphine; Cyclopropanes; Aziridines; Annulations; CATALYZED 4+2 ANNULATION; ASYMMETRIC-SYNTHESIS; DIMETHYLOXOSULFONIUM METHYLIDE; ALLYLIC COMPOUNDS; IMINO COMPOUNDS; DERIVATIVES; CHEMISTRY; CYCLOADDITION; EPOXIDATION; REACTIVITY;

D O I：

10.1016/j.tet.2009.10.099

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the presence of phosphite or phosphine, the reaction between 4-, 2-nitrobenzaldehyde and methylidenemalononitriles proceeded smoothly to give the cyclopropane derivatives in high yields, while the reaction between 4-, 2-benzaldehyde, and N-tosylbenzaldimines afforded the azidridine derivatives in moderate to high yields. A plausible mechanism was proposed and the strongly electron-withdrawing nitro-group is believed to play a critical role in these transformations. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：304 / 313

页数：10

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