Convenient preparative method of α,β-disubstituted cyclopentenone by zirconium promoted intermolecular coupling of an alkyne, EtMgBr (or ethylene) and CO

Tamotsu Takahashi, Zhenfeng Xi, Yasushi Nishihara, Shouquan Huo, Kayoko Kasai, Koichiro Aoyagi, Victor Denisov, Ei Ichi Negishi

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63 Citations (Scopus)

Abstract

Treatment of Cp2ZrCl2 with 2 equiv of EtMgBr in THF, followed by addition of an internal alkyne and subsequent treatment with CO/I2 gave α,β-disubstituted cyclopentenone in good to high yields. When a conjugated enyne was used as an alkyne component, α-alkenyl cyclopentenone was selectively formed in 80-89% yields. In the case of 4,6-decadiyne, α-alkynylcyclopentenone was formed in 88% yield. Bridged alkynes such as 1,4-dihexynylbenzene afforded α,α'-bridged cyclopentenone compounds in good yields.

Original languageEnglish
Pages (from-to)9123-9134
Number of pages12
JournalTetrahedron
Volume53
Issue number27
DOIs
Publication statusPublished - Jul 7 1997
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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