An efficient enantioselective fluorination of various β-ketoesters catalyzed chiral palladium complexes

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. Copyright © 2002 American Chemical Society.