Catalytic asymmetric epoxidation of stilbene using a chiral salen complex immobilized in Mn-exchanged Al-MCM-41

Paola Piaggio, Christopher Langham, Paul McMorn, Donald Bethell, Philip C. Bulman Page, Frederick E. Hancock, Chris Sly, Graham J. Hutchings

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Abstract

Manganese-exchanged Al-MCM-41 modified by the chiral salen ligand [(R,R)-(-)-N,N'-bis(3,5-di-tert-butylsalicylidene)cyclohexane-1,2-diamin e] can be used as an enantioselective heterogeneous epoxidation catalyst using iodosyl benzene as oxygen donor. Epoxidation of (Z)- and (E)-stilbene is studied in detail and experiments are described that demonstrate that the reaction is wholly catalysed heterogeneously. Similar enantioselectivity is observed for the oxidation of (Z)-stilbene to the (E)-epoxide using homogeneous (77.5% ee) or heterogeneous (70% ee) catalysts. The effect of temperature, solvents and donor ligands on the yield and enantioselection are discussed.
Original languageEnglish
Pages (from-to)143-148
Number of pages6
JournalJournal of the Chemical Society-Perkin Transactions 2
Volume1
DOIs
Publication statusPublished - 2000

Keywords

  • DESIGN
  • HYDROGENATION
  • MCM-41
  • ENANTIOSELECTIVE EPOXIDATION
  • UNFUNCTIONALIZED OLEFINS
  • OXIDATIONS

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