Palladium-catalyzed preparation of α-allyl esters and α,β-unsaturated esters from saturated esters via their silyl acetals

Jro Tsuji, Kazuhiko Takahashi, Ichiro Minami, Isao Shimizu

    Research output: Contribution to journalArticle

    54 Citations (Scopus)

    Abstract

    Reaction of ketene silyl acetals with allylic carbonates in the presence of palladium-phosphine catalyst in dioxane gives α-allyl esters in high yields. When the reaction is carried out with phosphine-free palladium catalyst in nitriles, α,β-unsaturated esters are obtained in good yields.

    Original languageEnglish
    Pages (from-to)4783-4786
    Number of pages4
    JournalTetrahedron Letters
    Volume25
    Issue number42
    DOIs
    Publication statusPublished - 1984

    Fingerprint

    phosphine
    Acetals
    Palladium
    Esters
    Nitriles
    Catalysts
    Carbonates

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

    Cite this

    Palladium-catalyzed preparation of α-allyl esters and α,β-unsaturated esters from saturated esters via their silyl acetals. / Tsuji, Jro; Takahashi, Kazuhiko; Minami, Ichiro; Shimizu, Isao.

    In: Tetrahedron Letters, Vol. 25, No. 42, 1984, p. 4783-4786.

    Research output: Contribution to journalArticle

    Tsuji, Jro ; Takahashi, Kazuhiko ; Minami, Ichiro ; Shimizu, Isao. / Palladium-catalyzed preparation of α-allyl esters and α,β-unsaturated esters from saturated esters via their silyl acetals. In: Tetrahedron Letters. 1984 ; Vol. 25, No. 42. pp. 4783-4786.
    @article{bb708f78bdf146d5b933309a31e0c44e,
    title = "Palladium-catalyzed preparation of α-allyl esters and α,β-unsaturated esters from saturated esters via their silyl acetals",
    abstract = "Reaction of ketene silyl acetals with allylic carbonates in the presence of palladium-phosphine catalyst in dioxane gives α-allyl esters in high yields. When the reaction is carried out with phosphine-free palladium catalyst in nitriles, α,β-unsaturated esters are obtained in good yields.",
    author = "Jro Tsuji and Kazuhiko Takahashi and Ichiro Minami and Isao Shimizu",
    year = "1984",
    doi = "10.1016/S0040-4039(01)81518-5",
    language = "English",
    volume = "25",
    pages = "4783--4786",
    journal = "Tetrahedron Letters",
    issn = "0040-4039",
    publisher = "Elsevier Limited",
    number = "42",

    }

    TY - JOUR

    T1 - Palladium-catalyzed preparation of α-allyl esters and α,β-unsaturated esters from saturated esters via their silyl acetals

    AU - Tsuji, Jro

    AU - Takahashi, Kazuhiko

    AU - Minami, Ichiro

    AU - Shimizu, Isao

    PY - 1984

    Y1 - 1984

    N2 - Reaction of ketene silyl acetals with allylic carbonates in the presence of palladium-phosphine catalyst in dioxane gives α-allyl esters in high yields. When the reaction is carried out with phosphine-free palladium catalyst in nitriles, α,β-unsaturated esters are obtained in good yields.

    AB - Reaction of ketene silyl acetals with allylic carbonates in the presence of palladium-phosphine catalyst in dioxane gives α-allyl esters in high yields. When the reaction is carried out with phosphine-free palladium catalyst in nitriles, α,β-unsaturated esters are obtained in good yields.

    UR - http://www.scopus.com/inward/record.url?scp=0001041487&partnerID=8YFLogxK

    UR - http://www.scopus.com/inward/citedby.url?scp=0001041487&partnerID=8YFLogxK

    U2 - 10.1016/S0040-4039(01)81518-5

    DO - 10.1016/S0040-4039(01)81518-5

    M3 - Article

    AN - SCOPUS:0001041487

    VL - 25

    SP - 4783

    EP - 4786

    JO - Tetrahedron Letters

    JF - Tetrahedron Letters

    SN - 0040-4039

    IS - 42

    ER -