Highly diastereoselective 1,3-dipolar cycloaddition via in situ formed ketimine ylides

被引：4

作者：

Cheng, Yu ^{[1
]}

Liu, Ya-Nan ^{[1
]}

Ye, Jia ^{[1
]}

He, Long ^{[1
]}

Kang, Tai-Ran ^{[1
]}

Liu, Quan-Zhong ^{[1
]}

机构：

[1] China W Normal Univ, Coll Chem & Chem Engn, Chem Synth & Pollut Control Key Lab Sichuan Prov, Nanchang 637009, Peoples R China

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 50期

基金：

中国国家自然科学基金;

关键词：

1,3-Dipolar cycloaddition; Ketimine ylides; Glycine ester; beta; gamma-Unsaturated keto ester; SELECTIVE 3+2 CYCLOADDITION; AZOMETHINE YLIDES; MULTICOMPONENT REACTIONS; CONSTRUCTION; DERIVATIVES; ANNULATION; CATALYSTS; LIGANDS; ESTERS;

D O I：

10.1016/j.tetlet.2012.09.138

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,3-Dipolar cycloaddition of conjugated unsaturated ketimine ylides was disclosed. The reaction of glycine ester with a series of beta,gamma-unsaturated keto esters in the presence of catalytic amount of TFA was found to give structurally diverse and functionally enriched pyrrolidine derivatives 3 in up to 88% yield. These processes feature a hydrolysis of glycine ketimine. A preliminary enantioselective version of the transformation was also investigated. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：6775 / 6778

页数：4

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