Asymmetric fluorination of β-keto esters catalyzed by chiral rare earth perfluorinated organophosphates

Shoko Suzuki, Hiroshi Furuno, Yasuo Yokoyama, Junji Inanaga

    Research output: Contribution to journalArticlepeer-review

    72 Citations (Scopus)

    Abstract

    Novel chiral rare earth metal complexes bearing perfluorinated binaphthyl phosphate ligand RE[(R)-F8BNP]3 (RE = rare earth; F8BNP = 5,5′,6,6′,7,7′,8,8′-octafluoro-1,1′-binaph thyl-2,2′-diyl phosphate) have been synthesized and used as a catalyst for the asymmetric electrophilic fluorination reaction of β-keto esters. The use of Sc[(R)-F8BNP]3 catalyst in combination with 1-fluoropyridinium triflate (NFPY-OTf) as a fluorinating agent was found to give the desired α-fluoro-β-keto esters in high chemical yields and enantiomeric excesses (up to 88% ee) under mild conditions.

    Original languageEnglish
    Pages (from-to)504-507
    Number of pages4
    JournalTetrahedron Asymmetry
    Volume17
    Issue number4
    DOIs
    Publication statusPublished - Feb 20 2006

    All Science Journal Classification (ASJC) codes

    • Catalysis
    • Physical and Theoretical Chemistry
    • Organic Chemistry
    • Inorganic Chemistry

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