Enantioselective synthesis of chiral tripodal cage compounds by [2 + 2 + 2] cycloaddition of branched triynes

Takanori Shibata, Toshifumi Uchiyama, Kohei Endo

    Research output: Contribution to journalArticle

    42 Citations (Scopus)

    Abstract

    Cyclotrimerization of triynes branched by a nitrogen atom of 2-aminophenol yielded planar-chiral tripodal cage compounds. When a cationic Rh-Me-DUPHOS catalyst was used, the cycloadducts were obtained in high yield and excellent ee, and a macrocyclic compound with a [15]cyclophane system was also obtained. This method can be further applied to the synthesis of a triarmed pyridinophane by the intramolecular reaction of a diyne-nitrile.

    Original languageEnglish
    Pages (from-to)3906-3908
    Number of pages3
    JournalOrganic Letters
    Volume11
    Issue number17
    DOIs
    Publication statusPublished - 2009 Sep 3

    Fingerprint

    Macrocyclic Compounds
    Nitriles
    Cycloaddition
    nitriles
    Cycloaddition Reaction
    cycloaddition
    nitrogen atoms
    Nitrogen
    catalysts
    Atoms
    Catalysts
    synthesis
    2-aminophenol

    ASJC Scopus subject areas

    • Organic Chemistry
    • Physical and Theoretical Chemistry
    • Biochemistry

    Cite this

    Enantioselective synthesis of chiral tripodal cage compounds by [2 + 2 + 2] cycloaddition of branched triynes. / Shibata, Takanori; Uchiyama, Toshifumi; Endo, Kohei.

    In: Organic Letters, Vol. 11, No. 17, 03.09.2009, p. 3906-3908.

    Research output: Contribution to journalArticle

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