Catalytic Asymmetric Mono-Fluorination of α-Keto Esters: Synthesis of Optically Active β-Fluoro-α-Hydroxy and β-Fluoro-α-Amino Acid Derivatives


  • This work was supported in part by a Grant-in-Aid for Scientific Research on a Priority Area (19028065, “Chemistry of Concert Catalysis”) and by Project Funding for Basic Science from RIKEN. We thank Dr. Daisuke Hashizume (RIKEN) for X-ray analyses of compounds syn-4 b, anti-4 b, and syn-5 b. We also thank the Takasago International Corporation for providing chiral ligands and the NIPPON ZEON Corporation for the generous gift of cyclopentyl methyl ether.


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Die enantioselektive Monofluorierung von α-Ketoestern gelang mithilfe eines mild basischen μ-Hydroxo-Palladiumkomplexes als Katalysator. Die anschließende Reduktion lieferte optisch aktive β-Fluor-α-hydroxyester, die in medizinisch relevante β-Fluor-α-aminoester überführt wurden.