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Enantioselective Synthesis of β,γ-Unsaturated α-Fluoroesters Catalyzed by N-Heterocyclic Carbenes

Authors

  • Dr. Yu-Ming Zhao,

    1. Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR (China)
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  • Man Sing Cheung,

    1. Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR (China)
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  • Prof. Dr. Zhenyang Lin,

    Corresponding author
    1. Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR (China)
    • Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR (China)
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  • Prof. Dr. Jianwei Sun

    Corresponding author
    1. Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR (China)
    • Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR (China)
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  • Financial support was provided by HKUST and Hong Kong RGC (GRF HKUST604411 and HKUST603711). We thank Prof. Liming Zhang (UCSB) for helpful discussions.

Abstract

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NHC trifft auf F: NHC-gebundene Enolate reagieren in einer katalytischen asymmetrischen Fluorierung zu β,γ-ungesättigten α-Fluorestern, die mit guter Effizienz und Stereoselektivität erhalten werden (siehe Schema; NFSI=N-Fluorbenzolsulfonimid). Mit dieser Strategie werden mögliche Probleme wie Fluorierung in γ-Position und Difluorierung umgangen. Experimentelle Befunde zusammen mit DFT-Rechnungen liefern Einblicke in den Reaktionsmechanismus.

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