title: Regioselective hydroarylations and parallel kinetic resolution of Vince lactam.
abstract: Two regioselective and complementary hydroarylation reactions of an unsymmetrical cyclic olefin have been developed. The products can be transformed in one step into constrained γ-amino acids. Regioselective arylation of Vince lactam is controlled by the choice of phosphine ligand enantiomer and the substituent on the amide nitrogen atom. The method was extended to a general regiodivergent parallel kinetic resolution of the racemic lactam.
authors: Worldwide Medicinal Chemistry, Pfizer Inc. Eastern Point Road, Groton, CT 06340 (USA). adam.kamlet@pfizer.com.
authors: Adam S
authors: AS
authors: Kamlet
authors: Cathy
authors: C
authors: Préville
authors: Kathleen A
authors: KA
authors: Farley
authors: David W
authors: DW
authors: Piotrowski
mesh_terms: D002384:Catalysis; D007700:Kinetics; D007769:Lactams / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D007769:Lactams; D009942:Organometallic Compounds
keywords: Vince lactam; arylation; kinetic resolution; regioselectivity; rhodium