Tetrahedron

Oxygen transfer reactions from an oxaziridinium tetrafluoroborate salt to olefins

X Lusinchi, G Hanquet

Index: Lusinchi, Xavier; Hanquet, Gilles Tetrahedron, 1997 , vol. 53, # 40 p. 13727 - 13738

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Citation Number: 73

Abstract

Oxaziridinium 5 efficiently epoxidises olefins. It reacts as an electrophilic reagent and does not transfer its oxygen to deactivated double-bonds or carbonyl functions. Epoxidation of cyclic allylic acetates shows a remarkable diastereoselectivity leading to the syn isomer. We propose that the epoxidation reaction proceeds through a one-step process.