Reaction of dianions of acetoacetic esters with epibromohydrin derivatives: A novel synthesis of tetrahydrofuran derivatives and tetrahydropyran derivatives

Masahisa Nakada, Yukitaka Iwata, Masashi Takano

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

The dianion of the acetoacetic ester reacts with epibromohydrin derivatives to afford a mixture of (Z)-2-alkoxycarbonylmethylidenetetrahydrofuran derivative and (E)-2-alkoxycarbonylmethylidenetetrahydropyran derivative. The selective formation of the tetrahydrofuran derivative is achieved by the use of LiClO4 as the additive.

Original languageEnglish
Pages (from-to)9077-9080
Number of pages4
JournalTetrahedron Letters
Volume40
Issue number51
DOIs
Publication statusPublished - 1999 Dec 17

Keywords

  • Acetoacetic ester
  • Dianion
  • Epibromohydrin
  • Epoxide
  • Tetrahydrofuran
  • Tetrahydropyran

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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