SilverCatalyzed Cascade Carboxylation and Cyclization of Trimethyl(2-methylenebut-3-yn-1-yl)silane Derivatives

Kohei Sekine, Yuta Sadamitsu, Tohru Yamada

Research output: Contribution to journalArticlepeer-review

30 Citations (Scopus)


C-C bond-forming carboxylation and cyclization of trimethyl(2-methylenebut-3-yn-1-yl)silane derivatives and carbon dioxide was developed. Silver catalysts and CsF promoted the reaction to afford the corresponding 2-furanone and 2-pyrone derivatives in good-to-high yields. The structure of the 2-furanone was confirmed by single-crystal X-ray crystallography, which revealed that the geometry of the exo-olefin was that of a Z-isomer. When an aromatic ring-substituted alkyne was used, 2-furanone derivatives were selectively obtained via 5-exo-dig cyclization, whereas the reaction of alkyl-substituted alkynes produced 2-pyrone derivatives with high selectivity.

Original languageEnglish
Pages (from-to)5706-5709
Number of pages4
JournalOrganic Letters
Issue number22
Publication statusPublished - 2015 Nov 20

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry


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