Asymmetric electrophilic amination of various carbon nucleophiles with enantiomerically pure chiral N-h oxaziridines derived from camphor and fenchone |
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Authors: | Bulman Page Philip C Limousin Corinne Murrell Victor L |
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Institution: | Department of Chemistry, Loughborough University, Leicestershire LE11 3TU, England. p.c.b.page@lboro.ac.uk |
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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. |
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