Asymmetric hydroarylation of norbornene derivatives catalyzed by palladium complexes of chiral quinolinyl-oxazolines

Chiral quinolinyl-oxazolines were found to be efficient ligands in the enantioselective palladium-catalyzed Heck-type hydroarylation of norbornene and its derivatives. The ligands with a medium sized alkyl group on the oxazoline ring provided higher enantioselectivities. The presence of elect ron-don ati ng substituents on the aryl iodide increased the selectivity and the yield of the reactions. The configuration of (-)-exo-2-phenylbicyclo[2.2.1]heptane has been assigned as (1R, 2'R). (C) 2001 Elsevier Science Ltd. All rights reserved.