Unusual Ester-Directed Regiochemical Control in endo-Selective Asymmetric 1,3-Dipolar Cycloadditions of Azomethine Ylides with β-Sulfonyl Acrylates

被引：36
|
作者：
Tong, Min-Chao [2 ]
Li, Jun [2 ]
Tao, Hai-Yan [2 ]
Li, Yu-Xue [1 ]
Wang, Chun-Jiang [1 ,2 ]
机构：
[1] Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 230032, Peoples R China
[2] Wuhan Univ, Coll Chem & Mol Sci, Wuhan 430072, Peoples R China
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2011年 / 17卷 / 46期
基金：
中国国家自然科学基金;
关键词：
asymmetric catalysis; cycloaddition; density functional calculations; diactivated alkenes; regioselectivity; ENANTIOSELECTIVE 3+2 CYCLOADDITION; 3-COMPONENT REACTION; DERIVATIVES; COMPLEXES; CATALYSTS; REVERSAL; LIGANDS;
D O I：
10.1002/chem.201102430
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Ester-controlled regioselectivity! A highly efficient, asymmetric 1,3-dipolar cycloaddition of azomethine ylides with unsymmetrically 1,2-diactivated sulfonyl acrylates has been developed, accompanied by an unusual regioselectivity that is controlled by the ester group rather than the sulfonyl group (see scheme). Theoretical calculations revealed a stepwise mechanism and rationalized the unusual ester-directed regioselectivity. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：12922 / 12927
页数：6
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