Rh-catalyzed alkene oxidation:: a highly efficient and selective process for preparing N-alkoxysulfonyl aziridines
Rh-catalyzed alkene oxidation:: a highly efficient and selective process for preparing N-alkoxysulfonyl aziridines
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DOI：
10.1016/j.tet.2006.07.099
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发表时间：
2006-12-04
期刊：
影响因子：
2.1
通讯作者：
Du Bois, J.
中科院分区：
文献类型：
--
作者：
Guthikonda, Kiran;Wehn, Paul M.;Du Bois, J.
通过选择性的烯烃分子内和分子间氧化反应，合成了独特的烷氧基磺酰基氮杂环化合物。这些方法是通用的，并且在低Rh-催化剂负载量（1- 2mol%）下有效地执行，仅略微过量的廉价商业氧化剂PhI（0Ac）（2）。对于分子间过程，三氯乙基氨基磺酸酯被确定为一种新的和显着有效的N-原子源，允许反应进行与烯烃底物的限量。氮丙啶产物易于亲核开环;这些方法具有区域选择性，可用于通过直接加入Me 2SO制备多官能化胺，包括α-氨基酮。(c)2006爱思唯尔有限公司保留所有权利。
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.