CuH-Catalyzed Enantioselective Reductive Coupling of 1,3-Dienes and Trifluoromethyl Ketoimines or α-Iminoacetates
Xue-Hua Deng, Jia-Xi Jiang, Qin Jiang, Ting Yang, Bo Chen, He Long, Wen‐Dao Chu, Cheng‐Yu He, Quan‐Zhong Liu
Abstract
The intermolecular addition of allylic copper species generated from diene and copper hydride remains elusive. Herein copper hydride catalyzed asymmetric cross reductive coupling of conjugated dienes and ketoimines including trifluoromethyl ketoimines and α-iminoacetates was first achieved using chiral Ph-BPE as the ligand, providing rapid access to structurally and optically enriched homoallylic amines containing two vicinal stereogenic centers with up to 95% yield, 99% ee, and 11:1 diastereoselectivities.
Topics & Concepts
ChemistryStereocenterTrifluoromethylAllylic rearrangementEnantioselective synthesisHydrideVicinalCopperCatalysisLigand (biochemistry)Intermolecular forceMedicinal chemistryYield (engineering)Combinatorial chemistryStereochemistryOrganic chemistryMoleculeAlkylMetalBiochemistryReceptorMaterials scienceMetallurgyCatalytic C–H Functionalization MethodsFluorine in Organic ChemistryAsymmetric Hydrogenation and Catalysis