- Asymmetric electrophilic amination of various carbon nucleophiles with enantiomerically pure chiral N-h oxaziridines derived from camphor and fenchone.
Asymmetric electrophilic amination of various carbon nucleophiles with enantiomerically pure chiral N-h oxaziridines derived from camphor and fenchone.
The Journal of organic chemistry (2002-10-26)
Philip C Bulman Page, Corinne Limousin, Victor L Murrell
PMID12398504
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.
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