Regioselective synthesis of highly substituted furans via tantalum-alkyne complexes.

Yasutaka Kataoka, Makoto Tezuka, Kazuhiko Takai, Kiitiro Utimoto

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

A variety of 2,3,4-trisubstituted furans are prepared by treatment of tantalum-alkyne complexes with a aldehydes followed by addition of an isocyanide in DME-PhH-THF (1:1:1). The regioselectivity of the reaction depends on the bulkiness of substituents on a acetylenes and the bulkier substituents tend to possess 4-position of the produced furans. 4-Trialkylsilyl-substitued furans are produced exclusively when trialkylsilylacetylenes are employed.

Original languageEnglish
Pages (from-to)3495-3502
Number of pages8
JournalTetrahedron
Volume48
Issue number17
DOIs
Publication statusPublished - 1992
Externally publishedYes

    Fingerprint

Keywords

  • Tantalum
  • furan
  • isocyanide
  • metal-alkyne complex
  • niobium

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this