Rh-catalyzed alkene oxidation:: a highly efficient and selective process for preparing N-alkoxysulfonyl aziridines

被引：106

作者：

Guthikonda, Kiran ^{[1
]}

Wehn, Paul M. ^{[1
]}

Caliando, Brian J. ^{[1
]}

Du Bois, J. ^{[1
]}

机构：

[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA

来源：

TETRAHEDRON | 2006年 / 62卷 / 49期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

D O I：

10.1016/j.tet.2006.07.099

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Unique alkoxysulfonyl aziridine heterocycles were prepared through selective intra- and intermolecular alkene oxidation reactions. These methods are general and perform efficiently at low Rh-catalyst loadings (1-2 mol %) with only a slight excess of an inexpensive commercial oxidant, PhI(OAc)(2). For intermolecular processes, trichloroethylsulfamate was identified as a novel and markedly effective N-atom source, allowing reactions to be conducted with limiting amounts of the olefin substrate. The aziridine products submit to facile, nucleophilic ring opening; these processes are regioselective and can be used to prepare polyfunctionalized amines, including alpha-aminoketones via the direct addition of Me2SO. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：11331 / 11342

页数：12

共 58 条

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