Reaction modes of oxidative dimerization of epoxycyclohexenols

Mitsuru Shoji, Satoshi Kishida, Yusuke Kodera, Isamu Shiina, Hideaki Kakeya, Hiroyuki Osada, Yujiro Hayashi

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

Of the 16 possible modes of the oxidation-6π-electrocylization-Diels-Alder reaction cascade for an epoxyquinone, and eight for a 2-alkenyl-3-hydroxymethyl-2-cyclohexen-1-one, only the endo-anti(epoxide)-anti(Me)-hetero and endo-anti(Me)-hetero are respectively observed, while both the endo-anti(epoxide)-anti(Me)-hetero and exo-anti(epoxide)-anti(Me)-homo reaction modes occur with epoxy-4-hydroxycyclohexenones owing to a hydrogen-bonding interaction.

Original languageEnglish
Pages (from-to)7205-7207
Number of pages3
JournalTetrahedron Letters
Volume44
Issue number38
DOIs
Publication statusPublished - 2003 Sep 15

Keywords

  • 6π-electrocylization
  • Diels-Alder reaction
  • Epoxyquinol
  • Hydrogen-bonding

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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