An efficient enantioselective fluorination of various beta-ketoesters catalyzed by chiral palladium complexes.J Am Chem Soc. 2002 Dec 11; 124(49):14530-1.JA
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 beta-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 alpha-fluoro beta-hydroxy and beta-amino acid derivatives, which should be extremely useful in developing novel drugs.