Asymmetric fluorination of β-keto esters catalyzed by chiral rare earth perfluorinated organophosphates |
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| Institution: | 1. School of Science, Harbin Institute of Technology, Shenzhen 518055, China;2. State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China;3. Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen 518055, China;4. School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin 150001, China |
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| 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′-binaphthyl-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. |
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