Lewis acid induced rearrangement of 2,3-epoxy amines; characterisation of aziridinium ion intermediates and regiospecific ring opening with nitrogen nucleophiles

Abstract

The Lewis acid induced isomerisation of 2,3-epoxy amines into the corresponding 2-trimethylsiloxymethylaziridinium ions is described; such intermediates have been characterised by ¹H NMR spectroscopy, and react with nitrogen nucleophiles regiospecifically to form 1-substituted 2, 3-diamino alcohols in good to excellent yields and with full stereochemical control.