Bis-sulfonyl ethylene as masked acetylene equivalent in catalytic asymmetric [3+2] cycloaddition of azomethine ylides

被引：107

作者：

Lopez-Perez, Ana ^{[1
]}

Adrio, Javier ^{[1
]}

Carretero, Juan C. ^{[1
]}

机构：

[1] Univ Autonoma Madrid, Fac Ciencias, Dept Quim Organ, E-28049 Madrid, Spain

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 31期

关键词：

D O I：

10.1021/ja804021m

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Enantioenriched 3-pyrrolines have been synthesized by highly enantioselective Fesulphos-Cu-catalysed 1,3-dipolar cycloaddition of azomethine ylides with trans-1,2-bisphenylsulfonyl ethylene, followed by reductive sulfonyl elimination. High levels of reactivity, exoselectivity, and enantioselectivity have been accomplished for a variety of substituted axomethine ylides. This cycloaddition desulfonylation strategy has been applied as a key step in the enantioselective synthesis of a biologically active C-azanucleoside.

引用

页码：10084 / +

页数：3

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