Tetrahedron letters

A synthesis of aziridines from α-iodoenones

MT Barros, CD Maycock, MR Ventura

Index: Barros, M. Teresa; Maycock, Christopher D.; Ventura, M. Rita Tetrahedron Letters, 2002 , vol. 43, # 24 p. 4329 - 4331

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Citation Number: 26

Abstract

Aziridines were prepared from α-iodocycloenones in very good yield, by a Michael addition/cyclisation (Gabriel–Cromwell) process employing a slight excess of primary amine and Cs2CO3 as base at 95° C. Using chiral amines it was possible to prepare optically pure aziridines. The same method was also efficient for the synthesis of aziridines from acyclic α- halounsaturated compounds. 2-Oxoazabicycles reacted with several nucleophiles to ...