Gold-catalyzed alkylation of silyl enol ethers with ortho-alkynylbenzoic acid esters

Haruo Aikawa, Tetsuro Kaneko, Naoki Asao, Yoshinori Yamamoto

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    8 Citations (Scopus)

    Abstract

    Unprecedented alkylation of silyl enol ethers has been developed by the use of ortho-alkynylbenzoic acid alkyl esters as alkylating agents in the presence of a gold catalyst. The reaction probably proceeds through the gold-induced in situ construction of leaving groups and subsequent nucleophilic attack on the silyl enol ethers. The generated leaving compound abstracts a proton to regenerate the silyl enol ether structure.

    Original languageEnglish
    Article number76
    Pages (from-to)648-652
    Number of pages5
    JournalBeilstein Journal of Organic Chemistry
    Volume7
    DOIs
    Publication statusPublished - 2011 May 20

    Keywords

    • Alkylation
    • Gold catalysis
    • Leaving group
    • Silyl enol ether
    • Substitution reaction

    ASJC Scopus subject areas

    • Organic Chemistry

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