Highly chemo-, enantio-, and regioselective synthesis of α,α-disubstituted furanones by Cu-catalyzed conjugate addition

Kohei Endo, Sayuri Yakeishi, Ryotaro Takayama, Takanori Shibata

    Research output: Contribution to journalArticle

    12 Citations (Scopus)

    Abstract

    A highly chemo-, enantio-, and regioselective synthesis of furanones bearing an α,α-disubstituted quaternary stereogenic center is reported. The Cu-catalyzed enantioselective conjugate addition of organoaluminum reagents to unsaturated ketoesters at room temperature and subsequent lactonization took place. Synthetic transformations of furanones represent facile approaches to various cyclic or acyclic compounds bearing a quaternary stereogenic center. Selective chemistry: A highly chemo-, enantio-, and regioselective synthesis of furanones bearing an α,α-disubstituted quaternary stereogenic center is reported (see scheme). Cu-catalyzed enantioselective conjugate addition of organoaluminum reagents to unsaturated ketoesters at room temperature and subsequent lactonization took place.

    Original languageEnglish
    Pages (from-to)8893-8897
    Number of pages5
    JournalChemistry - A European Journal
    Volume20
    Issue number29
    DOIs
    Publication statusPublished - 2014 Jul 14

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    Bearings (structural)
    Temperature

    Keywords

    • addition reactions
    • aluminum
    • asymmetric synthesis
    • copper
    • heterocyclic compounds

    ASJC Scopus subject areas

    • Chemistry(all)

    Cite this

    Highly chemo-, enantio-, and regioselective synthesis of α,α-disubstituted furanones by Cu-catalyzed conjugate addition. / Endo, Kohei; Yakeishi, Sayuri; Takayama, Ryotaro; Shibata, Takanori.

    In: Chemistry - A European Journal, Vol. 20, No. 29, 14.07.2014, p. 8893-8897.

    Research output: Contribution to journalArticle

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    abstract = "A highly chemo-, enantio-, and regioselective synthesis of furanones bearing an α,α-disubstituted quaternary stereogenic center is reported. The Cu-catalyzed enantioselective conjugate addition of organoaluminum reagents to unsaturated ketoesters at room temperature and subsequent lactonization took place. Synthetic transformations of furanones represent facile approaches to various cyclic or acyclic compounds bearing a quaternary stereogenic center. Selective chemistry: A highly chemo-, enantio-, and regioselective synthesis of furanones bearing an α,α-disubstituted quaternary stereogenic center is reported (see scheme). Cu-catalyzed enantioselective conjugate addition of organoaluminum reagents to unsaturated ketoesters at room temperature and subsequent lactonization took place.",
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    AU - Yakeishi, Sayuri

    AU - Takayama, Ryotaro

    AU - Shibata, Takanori

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    KW - heterocyclic compounds

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