The Diels-Alder reaction using a vinyl sulfoxide activated by the participation of a neighboring epoxide group

Hitoshi Abe, Daisuke Tsuchida, Setsuo Kashino, Yasuo Takeuchi, Takashi Harayama

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

A vinyl sulfoxide, which is considered to be a moderately reactive dienophile, could be activated by neighboring participation of an epoxide group. The Diels-Alder reaction of ortho-epoxyphenyl vinyl sulfoxide with cyclopentadiene in the presence of Yb(OTf)3 proceeded smoothly even at room temperature to afford the epoxy-opened cycloadducts with moderate stereoselectivity.

Original languageEnglish
Pages (from-to)833-837
Number of pages5
JournalChemical and Pharmaceutical Bulletin
Volume47
Issue number6
DOIs
Publication statusPublished - Jun 1999

Keywords

  • Diels-Alder reaction
  • Epoxide
  • Neighboring participation
  • Sulfonium salt
  • Vinyl sulfoxide

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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