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A Rapid Entry to Diverse γ‐Ylidenetetronate Derivatives through Regioselective ­Bromination of Tetronic Acid Derived γ‐Lactones and Metal‐Catalyzed Postfunctionalization

Abstract : The synthesis of a series of diverse methyl and benzyl γ‐ylidenetetronate derivatives was accomplished through the condensation of methyl and benzyl tetronates with (hetero)aryl aldehydes in a new two‐ or three‐step aldolisation/dehydration sequence. The bromination of methyl and benzyl γ‐ylidenetetronates occurred under mild conditions to provide the corresponding C‐3‐brominated γ‐unsaturated lactones. Di‐ and tribrominated γ‐lactones were prepared under slightly different conditions. Some brominated materials were employed in representative Stille, Suzuki–Miyaura, and Sonogashira cross‐coupling reactions to yield functionalized methyl and benzyl γ‐ylidenetetronate derivatives. Compounds that resulted from the Sonogashira cross‐coupling reactions were desilylated and converted into 1,2,3‐triazole derivatives through a copper(I)‐catalyzed 1,3‐dipolar cycloaddition reaction with benzyl azide.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02046144
Contributor : Madeleine Roux-Merlin <>
Submitted on : Friday, February 22, 2019 - 3:32:01 PM
Last modification on : Wednesday, July 8, 2020 - 12:42:24 PM

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N. Chopin, H. Yanai, S. Iikawa, G. Pilet, J.-P. Bouillon, et al.. A Rapid Entry to Diverse γ‐Ylidenetetronate Derivatives through Regioselective ­Bromination of Tetronic Acid Derived γ‐Lactones and Metal‐Catalyzed Postfunctionalization. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2015, 2015 (28), pp.6259-6269. ⟨10.1002/ejoc.201500663⟩. ⟨hal-02046144⟩

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