An Efficient Nickel-Catalyzed Asymmetric Oxazole-Forming Ugi-Type Reaction for the Synthesis of Chiral Aryl-Substituted THIQ Rings

Abstract

A nickel-catalyzed asymmetric oxazole-forming Ugi reaction of C,N-cyclic azomethine imines and isonitriles is disclosed. The reported protocol proceeds smoothly, and gives the corresponding adducts, which contain two important pharmaceutically active ring-systems (tetrahydroquinoline and oxazole rings), in good yields and excellent enantioselectivities by employing an easily accessible chiral diamine as a ligand. This simple and efficient strategy provides easy access to a series of C1-substituted aryl tetrahydroisoquinolines.

Keywords: chirality; nickel; oxazole; tetrahydroquinoline; ugi reaction.