Tetrahedron

Optically pure trans-2, 3-disubstituted N-sulfinyl aziridines. Regio-and stereoselective opening mediated by the sulfinyl group

…, M Santos, MA Sanz-Tejedor, JL García-Ruano

Index: Arroyo, Yolanda; Meana, Angela; Rodriguez, J. Felix; Santos, Mercedes; Sanz-Tejedor, M. Ascension; Garcia Ruano, Jose L. Journal of Organic Chemistry, 2005 , vol. 70, # 10 p. 3914 - 3920

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Citation Number: 17

Abstract

A new entry to optically pure trans-2, 3-disubstituted N-sulfinyl aziridines starting from 1, 2- aminosulfides, involving formation of a sulfonium salt intermediate followed by intramolecular nucleophilic attack by the sulfinamide nitrogen atom, is reported. The regio- and stereoselective opening of the aziridine ring can be achieved by anchimeric assistance of the sulfinyl group.