Iridium-catalyzed consecutive and enantioselective [2+2+2] cycloaddition of tetraynes and hexaynes for the construction of an axially chiral biaryl system

Takanori Shibata, Shiho Yoshida, Yoshikazu Arai, Maiko Otsuka, Kohei Endo

    Research output: Contribution to journalArticle

    46 Citations (Scopus)

    Abstract

    A chiral iridium complex catalyzed a consecutive and enantioselective [2+2+2] cycloaddition of polyynes to give axially chiral compounds. Intermolecular reaction of tetraynes, possessing aryl groups on their termini, with protected but-2-yne-1,4-diols gave C2-symmetrical quateraryl compounds. Intramolecular reaction of hexaynes, possessing aryl or alkyl groups on their termini gave C2-symmetrical biaryl compounds. The catalytic synthesis of a pentacene derivative with axial chiralities is also discussed.

    Original languageEnglish
    Pages (from-to)821-830
    Number of pages10
    JournalTetrahedron
    Volume64
    Issue number5
    DOIs
    Publication statusPublished - 2008 Jan 28

    Fingerprint

    Polyacetylenes
    Iridium
    Cycloaddition
    Chirality
    Cycloaddition Reaction
    Derivatives
    pentacene

    Keywords

    • Axial chirality
    • Biaryls
    • Cycloaddition
    • Enantioselective
    • Iridium

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

    Cite this

    Iridium-catalyzed consecutive and enantioselective [2+2+2] cycloaddition of tetraynes and hexaynes for the construction of an axially chiral biaryl system. / Shibata, Takanori; Yoshida, Shiho; Arai, Yoshikazu; Otsuka, Maiko; Endo, Kohei.

    In: Tetrahedron, Vol. 64, No. 5, 28.01.2008, p. 821-830.

    Research output: Contribution to journalArticle

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    AU - Yoshida, Shiho

    AU - Arai, Yoshikazu

    AU - Otsuka, Maiko

    AU - Endo, Kohei

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