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First Stereospecific Synthesis of ( E )- or ( Z )-α-Fluoroenones via a Kinetically Controlled Negishi Coupling Reaction

Abstract : A highly stereospecific synthesis of (E)- or (Z)-alpha-fluoro-alpha,beta-unsaturated ketones 4, via a kinetically controlled Negishi palladium-catalyzed coupling reaction, was developed, providing an easy and general access to valuable fluorinated intermediates (pharmaceutical, peptide mimic, and so on). The synthesis involved a reaction between E/Z gem-bromofluoroolefins 2 and alkoxyvinylzinc species 6 under controlled reaction temperature. At 10 degrees C, (Z)-4 (70 to 99% yields) was obtained along with unreacted (Z)-2 (66 to 99% yields). At THF reflux, the recovered olefin was transformed into (E)-4 (up to 98% yield).
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02384476
Contributor : Samuel Couve-Bonnaire <>
Submitted on : Thursday, November 28, 2019 - 1:48:25 PM
Last modification on : Monday, July 6, 2020 - 11:43:31 AM

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Guillaume Dutheuil, Clotilde Paturel, Xinsheng Lei, Samuel Couve-Bonnaire, Xavier Pannecoucke. First Stereospecific Synthesis of ( E )- or ( Z )-α-Fluoroenones via a Kinetically Controlled Negishi Coupling Reaction. Journal of Organic Chemistry, American Chemical Society, 2006, 71 (11), pp.4316-4319. ⟨10.1021/jo0604787⟩. ⟨hal-02384476⟩

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