An Efficient Enantioselective Fluorination of Various β-Ketoesters Catalyzed by Chiral Palladium Complexes

Abstract

Reflecting the importance of fluorinated organic compounds in medicinal chemistry, development of an efficient method for catalytic enantioselective fluorination is increasingly desirable. Using a novel palladium complex 2 (1−2.5 mol %), various β-ketoesters including cyclic and acyclic substrates were fluorinated with excellent enantioselectivity in the range of 83−94% ee. It is environmentally advantageous that this reaction proceeds well in solvents such as EtOH, rather than usual organic solvents. Furthermore, the product was successfully tranformed into both α-fluoro β-hydroxy and β-amino acid derivatives, which should be extremely useful in developing novel drugs.