New pinene-derived pyridines as bidentate chiral ligands

A synthesis of new bidentate pyridines has been developed, starting from ?-pinene. A copper complex of the pyridine-oxazoline ligands catalyzes asym. allylic oxidn. of cyclic olefins with good conversion rates and acceptable enantioselectivity (?67% ee). The imidazolium salt I has been identified as a precursor of the N,N'-unsym. N-heterocyclic carbene ligand, which upon complexation with palladium, catalyzed the intramol. amide enolate ?-arylation leading to oxindole in excellent yield but with low enantioselectivity.