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Iminium Salt-Catalysed Asymmetric Epoxidation using Hydrogen Peroxide as Stoichiometric Oxidant

  1. Philip C. Bulman Page1,
  2. Phillip Parker2,
  3. Gerasimos A. Rassias3,
  4. Benjamin R. Buckley2,
  5. Donald Bethell4

Article first published online: 24 JUL 2008

DOI: 10.1002/adsc.200800303

Issue

Advanced Synthesis & Catalysis

Advanced Synthesis & Catalysis

Volume 350, Issue 11-12, pages 1867–1874, August 4, 2008

Additional Information

How to Cite

Page, P. C. B., Parker, P., Rassias, G. A., Buckley, B. R. and Bethell, D. (2008), Iminium Salt-Catalysed Asymmetric Epoxidation using Hydrogen Peroxide as Stoichiometric Oxidant. Adv. Synth. Catal., 350: 1867–1874. doi: 10.1002/adsc.200800303

Author Information

  1. 1

    School of Chemical Sciences & Pharmacy, University of East Anglia, Norwich, Norfolk NR4 7TJ, U.K. Fax: (+44)-(0)1603-593008

  2. 2

    Department of Chemistry, Loughborough University, Loughborough, Leicestershire LE11 3TU, U.K.

  3. 3

    GlaxoSmithKline, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, U.K.

  4. 4

    Robert Robinson Laboratories, Department of Chemistry, University of Liverpool, P O Box 147, Liverpool L69 3BX, U.K.

Publication History

  1. Issue published online: 31 JUL 2008
  2. Article first published online: 24 JUL 2008
  3. Manuscript Revised: 18 JUN 2008
  4. Manuscript Received: 14 MAY 2008

Funded by

  • EPSRC
  • GlaxoSmithKline

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Keywords:

  • catalysis;
  • epoxidation;
  • iminium salts;
  • organocatalysis;
  • peroxides

Abstract

Iminium salt organocatalysts can provide high selectivity and high efficiency in catalytic asymmetric epoxidation. They are normally used in conjunction with Oxone as the stoichiometric oxidant. Oxone, however, has limited stability and is insoluble in most organic solvents; we report here for the first time the development of a reaction system driven by hydrogen peroxide as the stoichiometric oxidant, involving an unusual double catalytic cycle.

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