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  • Title: A Regioselective, One-Pot, Transition-Metal-Free α-Alkylation of Quinone Monoacetals for Various Organic Transformations.
    Author: Sharma P, Vishwakarma R, Rakheja R, Pasricha S, Hazra CK.
    Journal: Org Lett; 2024 Nov 05; ():. PubMed ID: 39498640.
    Abstract:
    Regioselective reactions of biologically significant quinones are challenging. An unprecedented advancement in quinone monoacetal (QMA) chemistry is proposed for constructing regioselective and less explored α-alkylated QMAs through the Morita-Baylis-Hillman (MBH) reaction. Electrophilic QMAs were transformed to nucleophilic umpolung reagents for aldol-type condensation with several electrophiles. Mechanistic studies reveal that solvent (TFE:water (1:1)) and in situ-generated potassium acetate accelerate the reaction. The ensuing MBH adducts were scalable and underwent several post-synthetic transformations and late-stage functionalization.
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