Lewis acid-mediated intramolecular addition of silyl enol ethers to internal unactivated alkynes

Ken Ichiro Imamura, Eiji Yoshikawa, Vladimir Gevorgyan, Tomoko Sudo, Naoki Asao, Yoshinori Yamamoto

    Research output: Contribution to journalArticlepeer-review

    18 Citations (Scopus)

    Abstract

    The EtAlCl2-mediated intramolecular addition of silyl enol ethers to both terminal and internal unactivated alkynes, bearing alkyl and phenyl susbstituents at the alkyne moiety, gave mono- and bicyclic β,γ-unsaturated ketones in good to excellent yields. On the other hand, the silyloxy-substituted cyclic vinylsilanes were obtained in moderate to high yields when the reactions were catalyzed by B(C6F5)3 in the presence of triethylsilane. All the reactions proceeded via endo-fashion exclusively. The mechanisms of these regiospecific Lewis acid-assisted carbocyclizations are proposed.

    Original languageEnglish
    Pages (from-to)1624-1631
    Number of pages8
    JournalCanadian Journal of Chemistry
    Volume79
    Issue number11
    DOIs
    Publication statusPublished - 2001 Jan 1

    Keywords

    • Alkynes
    • Carbocyclization
    • Lewis acid
    • Silyl enol ethers

    ASJC Scopus subject areas

    • Catalysis
    • Chemistry(all)
    • Organic Chemistry

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