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

J. Gullick, S. Taylor, P. McMorn, D. Bethell, P. C. B. Bulman Page, F. E. Hancock, F. King, G. J. Hutchings

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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.
Original languageEnglish
Pages (from-to)571-575
Number of pages5
JournalJournal of Molecular Catalysis A: Chemical
Volume182
Issue number1
Publication statusPublished - 2002

Keywords

  • OLEFINS
  • ANISOLE
  • styrene aziridination
  • donors
  • SOLID SOLVENTS
  • ZEOLITE CATALYSTS
  • FINE CHEMICALS SYNTHESIS
  • nitrene
  • bis(oxazoline)-modified CuHY zeolite

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