Additive Pummerer reaction of heteroaromatic sulfilimines with carbon nucleophiles

被引：46

作者：

Padwa, A ^{[1
]}

Nara, S ^{[1
]}

Wang, Q ^{[1
]}

机构：

[1] Emory Univ, Dept Chem, Atlanta, GA 30322 USA

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 04期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/j.tetlet.2005.11.026

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The additive Pummerer reaction of several heteroaromatic sulfilimines has been investigated. The overall process involves the reaction of the sulfilimine with TFAA to produce a transient N-tosyl-N-trifluoroacetyl sulfonium ion. Nucleophilic attack at the adjacent vinyl carbon results in the ejection of the sulfonamide group and the resulting thionium, ion loses a proton to give the observed product. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：595 / 597

页数：3

共 26 条

[21]

Padwa A, 1997, SYNTHESIS-STUTTGART, P1353

[22] Cyclic vinyl p-tolyl sulfilimines as chiral dienophiles:: Diels-Alder reactions with furan and acyclic dienes [J].