Reaction of dianions of acetoacetic esters with epibromohydrin derivatives: A novel synthesis of tetrahydrofuran derivatives and tetrahydropyran derivatives

Masahisa Nakada, Yukitaka Iwata, Masashi Takano

    Research output: Contribution to journalArticle

    22 Citations (Scopus)

    Abstract

    The dianion of the acetoacetic ester reacts with epibromohydrin derivatives to afford a mixture of (Z)-2-alkoxycarbonylmethylidenetetrahydrofuran derivative and (E)-2-alkoxycarbonylmethylidenetetrahydropyran derivative. The selective formation of the tetrahydrofuran derivative is achieved by the use of LiClO4 as the additive.

    Original languageEnglish
    Pages (from-to)9077-9080
    Number of pages4
    JournalTetrahedron Letters
    Volume40
    Issue number51
    Publication statusPublished - 1999 Dec 17

    Fingerprint

    Esters
    Derivatives
    tetrahydrofuran
    lithium perchlorate

    Keywords

    • Acetoacetic ester
    • Dianion
    • Epibromohydrin
    • Epoxide
    • Tetrahydrofuran
    • Tetrahydropyran

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

    Cite this

    Reaction of dianions of acetoacetic esters with epibromohydrin derivatives : A novel synthesis of tetrahydrofuran derivatives and tetrahydropyran derivatives. / Nakada, Masahisa; Iwata, Yukitaka; Takano, Masashi.

    In: Tetrahedron Letters, Vol. 40, No. 51, 17.12.1999, p. 9077-9080.

    Research output: Contribution to journalArticle

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