Asymmetric organocatalysis of epoxidation by iminium salts under non-aqueous conditions

P. C. B. Bulman Page, B. R. Buckley, D. Barros, A. J. Blacker, B. A. Marples, M. R. J. Elsegood

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Abstract

Three iminium salts have been tested as catalysts for the asymmetric epoxidation of simple alkenes under non-aqueous conditions in various solvents, at varying temperatures, employing tetraphenylphosphonium monoperoxybisulfate (TPPP) as the stoichiometric oxidant. Enantiomeric excesses of up to 89% have been observed. (c) 2007 Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)5386-5393
Number of pages8
JournalTetrahedron
Volume63
Issue number25
DOIs
Publication statusPublished - 2007

Keywords

  • CATALYSTS
  • ENANTIOSELECTIVE OLEFIN EPOXIDATION
  • ALKENE
  • UNSATURATED OXAZIRIDINES
  • OXONE(R)
  • MECHANISM
  • CHIRAL OXAZIRIDINIUM SALT
  • OXIDATION
  • OXYGEN-TRANSFER
  • EPOXIDATION
  • INTRAMOLECULAR EPOXIDATION

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