67 research outputs found

    Vinylogous Reactivity of Oxindoles Bearing Nonsymmetric 3‑Alkylidene Groups

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    The γ-functionalization of oxindoles bearing nonsymmetric 3-alkylidene groups via vinylogous Michael-type addition to nitroolefins was realized. The suppression of the interconversion between the <i>E</i> and <i>Z</i> isomers of the starting oxindoles allowed a site-specific diastereoselective and enantioselective transformation. Specific experiments allowed us to establish the rate-determining step of the reaction and to advance a robust hypothesis for the exclusive formation of an <i>s-cis</i> enolate as the only reactive intermediate
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