Catalytic Oxygenative Allylic Transposition of Alkenes into Enones with an Azaadamantane-Type Oxoammonium Salt Catalyst

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Abstract

The first catalytic oxygenative allylic transposition of unactivated alkenes into enones has been developed using an oxoammonium salt as the catalyst. This reaction converts various tri- and trans-disubstituted alkenes into their corresponding enones with transposition of their double bonds at ambient temperature in good yields. The use of a less-hindered azaadamantane-type oxoammonium salt as the catalyst and a combination of two distinct stoichiometric oxidants, namely, iodobenzene diacetate and magnesium monoperoxyphthalate hexahydrate (MMPP⋅6 H2O) are essential to facilitate the enone formation efficiently.

Original languageEnglish
Pages (from-to)10276-10279
Number of pages4
JournalChemistry - A European Journal
Volume23
Issue number43
DOIs
Publication statusPublished - 2017 Aug 1

Keywords

  • alkenes
  • enones
  • organocatalysis
  • oxygenation
  • synthetic methods

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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