Cobalt‐Catalyzed Efficient Convergent Asymmetric Hydrogenation of <i>E</i>/<i>Z</i>‐Enamides
Tiantian Chen, Yashi Zou, Yanhua Hu, Zhenfeng Zhang, Hao Wei, Liangming Wei, Wanbin Zhang
Abstract
Using the diphosphine-cobalt-zinc catalytic system, an efficient asymmetric hydrogenation of internal simple enamides has been realized. In particular, the Ph-BPE ligand can achieve convergent asymmetric hydrogenation of E/Z-substrates. High yields and excellent enantioselectivities were obtained for both acyclic and cyclic enamides bearing α-alkyl-β-aryl, α-aryl-β-aryl, and α-aryl-β-alkyl substituents. Hydrogenated products can be applied for the synthesis of useful chiral drugs such as Arfromoterol, Rotigotine, and Norsertraline. In addition, reasonable catalytic mechanism and stereocontrol mode are proposed based on DFT calculations.
Topics & Concepts
ArylCatalysisCobaltAlkylChemistryAsymmetric hydrogenationCombinatorial chemistryLigand (biochemistry)ZincCatalytic hydrogenationMedicinal chemistryOrganic chemistryEnantioselective synthesisReceptorBiochemistryAsymmetric Hydrogenation and CatalysisSurface Chemistry and CatalysisCarbon dioxide utilization in catalysis