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

Abstract

The title bipyridine ligand (+)-6(PINDY), prepared in five steps from (-)-beta-pinene, forms a stable complex with CuCl(2) (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, approximately 30 min, 49-75% ee).