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

Research output: Contribution to journalArticle

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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

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Alkynes
Carbon Monoxide
Bridged-Ring Compounds
cyclopentenone
ethylene

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Convenient preparative method of α,β-disubstituted cyclopentenone by zirconium promoted intermolecular coupling of an alkyne, EtMgBr (or ethylene) and CO. / Takahashi, Tamotsu; Xi, Zhenfeng; Nishihara, Yasushi; Huo, Shouquan; Kasai, Kayoko; Aoyagi, Koichiro; Denisov, Victor; Negishi, Ei Ichi.

In: Tetrahedron, Vol. 53, No. 27, 07.07.1997, p. 9123-9134.

Research output: Contribution to journalArticle

Takahashi, Tamotsu ; Xi, Zhenfeng ; Nishihara, Yasushi ; Huo, Shouquan ; Kasai, Kayoko ; Aoyagi, Koichiro ; Denisov, Victor ; Negishi, Ei Ichi. / Convenient preparative method of α,β-disubstituted cyclopentenone by zirconium promoted intermolecular coupling of an alkyne, EtMgBr (or ethylene) and CO. In: Tetrahedron. 1997 ; Vol. 53, No. 27. pp. 9123-9134.
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AU - Takahashi, Tamotsu

AU - Xi, Zhenfeng

AU - Nishihara, Yasushi

AU - Huo, Shouquan

AU - Kasai, Kayoko

AU - Aoyagi, Koichiro

AU - Denisov, Victor

AU - Negishi, Ei Ichi

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