Tetrahedron

One step synthesis of aziridines by the Michael type addition of free sulfimides: Preparation and absolute configuration of optically active acylaziridines

N Furukawa, T Yoshimura, M Ohtsu, T Akasaka, S Oae

Index: Furukawa, Naomichi; Yoshimura, Toshiaki; Ohtsu, Masami; Akasaka, Takeshi; Oae, Shigeru Tetrahedron, 1980 , vol. 36, # 1 p. 73 - 80

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Citation Number: 44

Abstract

The Michael type additions of diphenyl N-unsubstituted sulfimide (free sulfimide) to various electrophilic olefins were carried out. The reaction with cis-and trans-dibenzoylethylene, dimethyl-fumarate, dimethylmaleate, benzalacetophenone and benzalacetone gave mainly the corresponding trans-2-acylaziridines and trans-enaminoketones. However, phenyl vinyl sulfone or acrylonitrile afforded not the corresponding aziridine but diphenyl-N-2-cyano or ...