Asymmetric Electrophilic Amination of Various Carbon Nucleophiles with Enantiomerically Pure Chiral NH Oxaziridines Derived from Camphor and Fenchone

PC Bulman Page, C Limousin…

Index: Page, Philip C. Bulman; Limousin, Corinne; Murrell, Victor L. Journal of Organic Chemistry, 2002 , vol. 67, # 22 p. 7787 - 7796

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Citation Number: 19

Abstract

The first two stable enantiomerically pure chiral NH 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 ...