A unique and highly efficient method for catalytic olefin aziridination

被引:211
作者
Guthikonda, K [1 ]
Du Bois, J [1 ]
机构
[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA
关键词
D O I
10.1021/ja028253a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A facile, high yielding, and stereospecific method for olefin aziridination is described. This process capitalizes on the unique reactivity of sulfamate esters in combination with 1-2 mol % Rh2(tfacam)4 and PhI(OAc)2 as the terminal oxidant to promote N-atom transfer reactions. A range of structurally and electronically disparate alkenes are found to react under conditions that employ substrate as the limiting reagent and only a slight excess of H2NSO3CH2CCl3 as the nitrogen source. The product alkoxysulfonyl aziridines are useful intermediates that react smoothly with nucleophiles to generate 1,2-amine derivatives. Following aziridine ring-opening, the N-trichloroethoxysulfonyl group can be removed under mild reductive conditions (Zn(Cu)/AcOH-MeOH) to give the corresponding 1° amine. The efficient and convenient performance of this chemistry should establish it as a useful tool for synthesis. Copyright © 2002 American Chemical Society.
引用
收藏
页码:13672 / 13673
页数:2
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