PINDY:  A Novel, Pinene-Derived Bipyridine Ligand and Its Application in Asymmetric, Copper(I)-Catalyzed Allylic Oxidation

The title bipyridine ligand (+)-6(PINDY), prepared in five steps from (−)-β-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, ∼30 min, 49−75% ee).