PINDY: A novel, pinene-derived bipyridine ligand and its application in asymmetric, copper(I)-catalyzed allylic oxidation

[GRAPHICS] The title bipyridine ligand (+)-6(PINDY), prepared in five steps from (-)-beta-pinene, forms a stable complex with CuCl2 (8) that has been characterized by X-ray crystallography to reveal an unusual geometry at Cu. Triflate 9 proved to catalyze asymmetric allylic oxidation (10 --> 11; rt, similar to 30 min, 49-75% ee).