Rhodium-catalyzed arylative cyclization of alkynones induced by addition of arylboronic acids

Tomoya Miura, Masahiko Shimada, Masahiro Murakami

Research output: Contribution to journalArticlepeer-review

36 Citations (Scopus)

Abstract

Alkynones react with arylboronic acids in the presence of a rhodium(I) catalyst to afford four- and five-membered-ring cyclic alcohols equipped with a tetrasubstituted exocyclic olefin. The cyclic allylic alcohol skeleton is constructed by the carbon-carbon bond formation between the carbonyl group and an alkenylrhodium(I) intermediate formed by the regioselective addition of an arylrhodium(I) species across the carbon-carbon triple bond.

Original languageEnglish
Pages (from-to)6131-6140
Number of pages10
JournalTetrahedron
Volume63
Issue number27
DOIs
Publication statusPublished - Jul 2 2007
Externally publishedYes

Keywords

  • Addition
  • Alkynone
  • Boron
  • Cyclization
  • Rhodium

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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