Highly enantioselective construction of a chiral spirocyclic structure by the [2 + 2 + 2] cycloaddition of diynes and exo-methylene cyclic compounds

Kyoji Tsuchikama, Yusuke Kuwata, Takanori Shibata

    Research output: Contribution to journalArticle

    66 Citations (Scopus)

    Abstract

    The enantioselective [2 + 2 + 2] cycloaddition of 1,6-diynes with α-methylene lactones and cyclic ketones gave various chiral spirocyclic compounds. The reaction proceeded with high enantioselectivity when the rhodium-xylylBINAP complex was used as a chiral catalyst. Not only exo-methylene cyclic compounds but also exo-methylene acyclic compounds could be used as coupling partners for diynes. The present protocol provides access to a new chiral library possessing a quaternary carbon center, including a spirocyclic system.

    Original languageEnglish
    Pages (from-to)13686-13687
    Number of pages2
    JournalJournal of the American Chemical Society
    Volume128
    Issue number42
    DOIs
    Publication statusPublished - 2006 Oct 25

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    Diynes
    Cycloaddition
    Enantioselectivity
    Cycloaddition Reaction
    Rhodium
    Ketones
    Catalysts
    Carbon

    ASJC Scopus subject areas

    • Chemistry(all)

    Cite this

    Highly enantioselective construction of a chiral spirocyclic structure by the [2 + 2 + 2] cycloaddition of diynes and exo-methylene cyclic compounds. / Tsuchikama, Kyoji; Kuwata, Yusuke; Shibata, Takanori.

    In: Journal of the American Chemical Society, Vol. 128, No. 42, 25.10.2006, p. 13686-13687.

    Research output: Contribution to journalArticle

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