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The catalytic enantioselective electrophilic fluorinations of active methine compounds promoted chiral palladium complexes have been developed. Treatment of β-keto phosphonates and β-ketoesters with N-fluorobenzenesulfonimide as the fluorine source under mild reaction conditions afforded the corresponding α-fluorinated adducts in high yields with excellent enantiomeric excesses (up to 99% ee). These reactions can be conducted in alcoholic solvents without any precaution to exclude water and moisture.

Enantioselective Fluorination of β-Keto Phosphonates and β-Ketoesters Catalyzed by Chiral Palladium Complexes