Asymmetric electrophilic Amination of various carbon nucleophiles with enantiomerically pure chiral N-H oxaziridines derived from camphor and fenchone

Bulman Page, P. C. B., Limousin, C. and Murrell, V. L. (2002) Asymmetric electrophilic Amination of various carbon nucleophiles with enantiomerically pure chiral N-H oxaziridines derived from camphor and fenchone. Journal of Organic Chemistry, 67 (22). pp. 7787-7796. ISSN 0022-3263

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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.

Item Type: Article
Uncontrolled Keywords: enantioselective amination,sulfides,reagents,amino-acid-derivatives,general-approach,1-oxides,beta-hydroxyesters,alpha-hydrazino acids,nitrogen,3-dithiane,alkylhydroxylamines,2-acyl-1
Faculty \ School: Faculty of Science > School of Chemistry
Depositing User: Rachel Smith
Date Deposited: 21 Jun 2011 10:19
Last Modified: 21 Apr 2020 20:43
URI: https://ueaeprints.uea.ac.uk/id/eprint/32839
DOI: 10.1021/jo020306j

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