Enantioselective intramolecular [2 + 2 + 2] cycloaddition of enediynes for the synthesis of chiral cyclohexa-1,3-dienes

Takanori Shibata, Hiroshi Kurokawa, Kazumasa Kanda

    Research output: Contribution to journalArticle

    41 Citations (Scopus)

    Abstract

    (Chemical Equation Presented) The enantioselective intramolecular [2 + 2 + 2] cycloaddition of various enediynes, where two acetylenic moieties are connected by a trans-olefinic moiety, gave chiral tricyclic cyclohexa-1,3-dienes using Rh-H8-BINAP catalyst. In the case of carbon-atom-tethered enediynes, enantioselectivity was generally good-to-high regardless of the substituents on their alkyne termini. In contrast, with heteroatom-tethered enediynes, appropriate substituents were required to induce the oxidative coupling of alkyne and alkene moieties before that of two alkyne moieties, which would be important for highly enantioselective intramolecular cycloaddition.

    Original languageEnglish
    Pages (from-to)6521-6525
    Number of pages5
    JournalJournal of Organic Chemistry
    Volume72
    Issue number17
    DOIs
    Publication statusPublished - 2007 Aug 17

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    Enediynes
    Alkynes
    Cycloaddition
    Enantioselectivity
    Alkenes
    Carbon
    Atoms
    Catalysts

    ASJC Scopus subject areas

    • Organic Chemistry

    Cite this

    Enantioselective intramolecular [2 + 2 + 2] cycloaddition of enediynes for the synthesis of chiral cyclohexa-1,3-dienes. / Shibata, Takanori; Kurokawa, Hiroshi; Kanda, Kazumasa.

    In: Journal of Organic Chemistry, Vol. 72, No. 17, 17.08.2007, p. 6521-6525.

    Research output: Contribution to journalArticle

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    abstract = "(Chemical Equation Presented) The enantioselective intramolecular [2 + 2 + 2] cycloaddition of various enediynes, where two acetylenic moieties are connected by a trans-olefinic moiety, gave chiral tricyclic cyclohexa-1,3-dienes using Rh-H8-BINAP catalyst. In the case of carbon-atom-tethered enediynes, enantioselectivity was generally good-to-high regardless of the substituents on their alkyne termini. In contrast, with heteroatom-tethered enediynes, appropriate substituents were required to induce the oxidative coupling of alkyne and alkene moieties before that of two alkyne moieties, which would be important for highly enantioselective intramolecular cycloaddition.",
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