Asymmetric epoxidation of chromenes mediated by iminium salts: Synthesis of mollugin and (3S,4R)-trans-3,4-dihydroxy-3,4-dihydromollugin

Philip C. Bulman Page, Yohan Chan, Abu Hassan Noor Armylisas, Mohammed Alahmdi

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Abstract

Organocatalytic asymmetric epoxidation of chromenes mediated by iminium salt catalysts under non-aqueous conditions provided ees as high as 99%. Contrastingly, reaction under aqueous conditions can form the corresponding diol products with ees as high as 71%. The process has been used for the synthesis of the East African medicinal plant metabolite (3S,4R)-trans-3,4-dihydroxy-3,4-dihydromollugin.
Original languageEnglish
Pages (from-to)8406–8416
JournalTetrahedron
Volume72
Issue number51
Early online date2 Nov 2016
DOIs
Publication statusPublished - 22 Dec 2016

Keywords

  • Asymmetric catalysis
  • Iminium salt
  • Enantioselective synthesis
  • Chromene
  • Mollugin

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