New synthetic methods for α,β -unsaturated ketones, aldehydes, esters and lactones by the palladium-catalyzed reactions of silyl enol ethers, ketene silyl acetals, and enol acetates with allyl carbonates

Ichiro Minami*, Kazuhiko Takahashi, Isao Shimizu, Tsuneo Kimura, Jiro Tsuji

*この研究の対応する著者

    研究成果: Article査読

    104 被引用数 (Scopus)

    抄録

    Silyl enol ethers and ketene silyl acetals derived from ketones, aldehydes, esters and lactones are converted into α,β-unsaturated ketones, aldehydes, esters and lactones by treatment with allyl carbonates in high yields using the palladium-bis(diphenylphosphino)ethane (dppe) complex as catalyst. Phosphine-free palladium catalyst instead of the palladium-phosphine complex gives a higher selectivity for the preparation of cyclopentenone, cyclooctenone, dienones, α,β-unsaturated esters and lactones. As a solvent, the use of nitriles such as acetonitrile is essential. In other solvents, allylation takes place. Enol acetates derived from ketones are converted into α,β-unsaturated ketones by reaction with allyl carbonate in acetonitrile using the palladium complex and tributyltin methoxide as bimetallic catalysts.

    本文言語English
    ページ(範囲)2971-2977
    ページ数7
    ジャーナルTetrahedron
    42
    11
    DOI
    出版ステータスPublished - 1986

    ASJC Scopus subject areas

    • 生化学
    • 有機化学
    • 創薬

    フィンガープリント

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