Heterogeneous aziridination of styrene using N-(p-nitrophenylsulfonyl)imino phenyliodinane as nitrene donor: influence of the reaction parameters on yield and enantioselectivity

Gullick, J., Taylor, S., McMorn, P., Bethell, D., Bulman Page, P. C. B., Hancock, F. E., King, F. and Hutchings, G. J. (2002) Heterogeneous aziridination of styrene using N-(p-nitrophenylsulfonyl)imino phenyliodinane as nitrene donor: influence of the reaction parameters on yield and enantioselectivity. Journal of Molecular Catalysis A: Chemical, 182 (1). pp. 571-575. ISSN 1381-1169

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Abstract

The copper-catalysed aziridination of styrene with copper-exchanged zeolite Y (CuHY) and copper(II) triflate (Cu(OTf)(2)) as catalysts is described and discussed. In particular, the effects of reaction conditions on the yield and enantiomeric excess of the aziridine product are described using [N-(p-nitrophenyisulfonyl)imino]phenyliodinane (PhI=NNs) as nitrene donor. By careful control of the styrene:nitrene donor molar ratio and the solvent, an ee of 95% can be obtained for the heterogeneously catalysed bis(oxazoline)-modified zeolite CuHY The ee achieved with the zeolite immobilised catalyst is significantly higher than that achieved for the non-immobilised homogeneous catalyst under comparable reaction conditions. (C) 2002 Elsevier Science B.V. All rights reserved.

Item Type: Article
Uncontrolled Keywords: olefins,anisole,styrene aziridination,donors,solid solvents,zeolite catalysts,fine chemicals synthesis,nitrene,bis(oxazoline)-modified cuhy zeolite
Faculty \ School: Faculty of Science > School of Chemistry
Depositing User: Rachel Smith
Date Deposited: 21 Jun 2011 10:47
Last Modified: 21 Apr 2020 20:46
URI: https://ueaeprints.uea.ac.uk/id/eprint/32833
DOI:

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