DBFOX-Ph/metal complexes: evaluation as catalysts for enantioselective fluorination of 3-(2-arylacetyl)-2-thiazolidinones.

We examined the catalytic enantioselective fluorination of 3-(2-arylacetyl)-2-thiazolidinones 1 with N-fluorobenzenesulfonimide (NFSI) by DBFOX-Ph/metal complexes under a variety of conditions. After optimization of the metal salts, solvents and additives, we found that the fluoro-2-thiazolidinones 2 were obtained in good to high yields with moderate to good enantioselectivities (up to 78% ee) when the reaction was carried out in the presence of DBFOX-Ph (11 mol%), Ni(ClO(4))(2).6H(2)O (10 mol%) and 2,6-lutidine (0 or 1.0 equiv) in CH(2)Cl(2).