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Catalytic Enantioselective Cyclopropanation of α-Fluoroacrylates: An Experimental and Theoretical Study

Abstract : Herein, we report the catalytic asymmetric synthesis of functionalized fluorocyclopropanes from α-fluoroacrylates. The method using Rh2((S)-TCPTTL)4 allowed the difficult reaction of an in situ-generated electrophilic Rh-carbene with an electron-poor α-fluoroacrylate. The desired fluorocyclopropanes were obtained in good yields, excellent dr and ee. Finally, the mechanism of this transformation was studied by density functional theory (DFT) calculations to explain the particular reactivity of the donor–acceptor diazo compounds with electron-deficient α-fluoroacrylates.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02278764
Contributor : Madeleine Roux-Merlin <>
Submitted on : Wednesday, September 4, 2019 - 3:50:01 PM
Last modification on : Wednesday, July 8, 2020 - 2:12:04 PM

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Amandine Pons, Vincent Tognetti, Laurent Joubert, Thomas Poisson, Xavier Pannecoucke, et al.. Catalytic Enantioselective Cyclopropanation of α-Fluoroacrylates: An Experimental and Theoretical Study. ACS Catalysis, American Chemical Society, 2019, 9 (3), pp.2594-2598. ⟨10.1021/acscatal.9b00354⟩. ⟨hal-02278764⟩

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