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Ru-Catalyzed Switchable Reactions of Acrylic Acids with Glyoxylate: Access to Functionalized γ-Butenolides

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    Ru-Catalyzed Switchable Reactions of Acrylic Acids with Glyoxylate: Access to Functionalized γ-Butenolides
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    Organic Letters

    Cite this: Org. Lett. 2024, 26, 50, 10658–10664
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    https://doi.org/10.1021/acs.orglett.4c03095
    Published December 8, 2024
    Copyright © 2024 American Chemical Society
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    Abstract

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    We herein report a switchable coupling of acrylic acids with ethyl glyoxylate under ruthenium catalysis enabling the synthesis of diverse functionalized γ-butenolides. The carboxyl-directed vinylic C–H cleavage and dual nucleophilic addition to aldehyde are achieved to deliver hydroxymethylated butanolides under mild and oxidant-free conditions. Alternatively, a controlled and unprecedented tandem C–H cyclization/oxidative homocoupling reaction is realized by using silver salt as the oxidant to generate a range of dimeric butenolides bearing vicinal all-carbon quaternary centers.

    Copyright © 2024 American Chemical Society

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    Organic Letters

    Cite this: Org. Lett. 2024, 26, 50, 10658–10664
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.4c03095
    Published December 8, 2024
    Copyright © 2024 American Chemical Society
    Request reuse permissions

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