Asymmetric electrophilic amination of various carbon nucleophiles with enantiomerically pure chiral N-h oxaziridines derived from camphor and fenchone.

Philip C Bulman Page, Corinne Limousin, Victor L Murrell

Index: J. Org. Chem. 67(22) , 7787-96, (2002)

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Abstract

The first two stable enantiomerically pure chiral N-H oxaziridines, derived from camphor and fenchone, are shown to act as electrophilic sources of nitrogen upon reaction with various carbon nucleophiles. Nitrogen is transferred, together with the camphor/fenchone unit, when deprotonated esters, malonates, and nitriles are used as nucleophiles. One of the ester or nitrile units in the substrate usually undergoes hydrolysis; a cyclic mechanism is proposed to account for this observation.