Enantioselective intramolecular [2 + 2 + 2] cycloaddition of 1,4-diene-ynes: A new approach to the construction of quaternary carbon stereocenters

Takanori Shibata, Yu Ki Tahara

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    47 Citations (Scopus)

    Abstract

    The intramolecular [2 + 2 + 2] cycloaddition of various 1,4-diene-ynes was examined using a chiral rhodium catalyst. In the case of 1,4-diene-ynes with a substituent at the 2-position of the 1,4-diene moiety, tricyclic compounds possessing a strained bicyclo[2.2.1]heptene skeleton with two quaternary carbon stereocenters were obtained in high enantiomeric excess. On the other hand, in the case of 1,4-diene-ynes with no substituent at this position, bicyclic cyclohexa-1,3-dienes with a quaternary carbon stereocenter were obtained probably by carbon-carbon bond cleavage of the reaction intermediate.

    Original languageEnglish
    Pages (from-to)11766-11767
    Number of pages2
    JournalJournal of the American Chemical Society
    Volume128
    Issue number36
    DOIs
    Publication statusPublished - 2006 Sep 13

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    Cycloaddition
    Cycloaddition Reaction
    Carbon
    Reaction intermediates
    Rhodium
    Skeleton
    Catalysts

    ASJC Scopus subject areas

    • Chemistry(all)

    Cite this

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    title = "Enantioselective intramolecular [2 + 2 + 2] cycloaddition of 1,4-diene-ynes: A new approach to the construction of quaternary carbon stereocenters",
    abstract = "The intramolecular [2 + 2 + 2] cycloaddition of various 1,4-diene-ynes was examined using a chiral rhodium catalyst. In the case of 1,4-diene-ynes with a substituent at the 2-position of the 1,4-diene moiety, tricyclic compounds possessing a strained bicyclo[2.2.1]heptene skeleton with two quaternary carbon stereocenters were obtained in high enantiomeric excess. On the other hand, in the case of 1,4-diene-ynes with no substituent at this position, bicyclic cyclohexa-1,3-dienes with a quaternary carbon stereocenter were obtained probably by carbon-carbon bond cleavage of the reaction intermediate.",
    author = "Takanori Shibata and Tahara, {Yu Ki}",
    year = "2006",
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    T1 - Enantioselective intramolecular [2 + 2 + 2] cycloaddition of 1,4-diene-ynes

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    AU - Shibata, Takanori

    AU - Tahara, Yu Ki

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    N2 - The intramolecular [2 + 2 + 2] cycloaddition of various 1,4-diene-ynes was examined using a chiral rhodium catalyst. In the case of 1,4-diene-ynes with a substituent at the 2-position of the 1,4-diene moiety, tricyclic compounds possessing a strained bicyclo[2.2.1]heptene skeleton with two quaternary carbon stereocenters were obtained in high enantiomeric excess. On the other hand, in the case of 1,4-diene-ynes with no substituent at this position, bicyclic cyclohexa-1,3-dienes with a quaternary carbon stereocenter were obtained probably by carbon-carbon bond cleavage of the reaction intermediate.

    AB - The intramolecular [2 + 2 + 2] cycloaddition of various 1,4-diene-ynes was examined using a chiral rhodium catalyst. In the case of 1,4-diene-ynes with a substituent at the 2-position of the 1,4-diene moiety, tricyclic compounds possessing a strained bicyclo[2.2.1]heptene skeleton with two quaternary carbon stereocenters were obtained in high enantiomeric excess. On the other hand, in the case of 1,4-diene-ynes with no substituent at this position, bicyclic cyclohexa-1,3-dienes with a quaternary carbon stereocenter were obtained probably by carbon-carbon bond cleavage of the reaction intermediate.

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