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Synfacts 2005(0): 0026-0026  
DOI: 10.1055/s-2005-865373
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Coupling of 1-Alkyl-2-(bromomethyl)aziri­-dines with Lithium Dialkylcuprates towards 1,2-Dialkylaziridines

Contributor(s): Victor Snieckus, Zhongdong Zhao
M. D’hooghe, M. Rottier, R. Jolie, N. De Kimpe*
Ghent University, Belgium
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Publication History

Publication Date:
20 July 2005 (online)

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Significance

This work constitutes the first report of a reaction between an organocuprate and a 1-alkyl-2-(bromomethyl)aziridines 1. Thus 1 may be considered as a synthetic equivalent of an aziridinylmethyl cation 2. A variety of substituted 1,2-dialkylaziridines are be obtained by this route. However, in a few cases, using bis(isopropenyl)cuprate and lithium bis(allyl)cuprate, allyl­amines resulting from ring opening were isolated in 40-78%.