Cinchona-Alkaloid-Derived NNP Ligand for Iridium-Catalyzed Asymmetric Hydrogenation of Ketones
Lin Zhang, Ling Zhang, Qian Chen, Lin Li, Jian Jiang, Hao Sun, Chong Zhao, Yuanyong Yang, Chun Li
Abstract
Most ligands applied for asymmetric hydrogenation are synthesized via multistep reactions with expensive chemical reagents. Herein, a series of novel and easily accessed cinchona-alkaloid-based NNP ligands have been developed in two steps. By combining [Ir(COD)Cl]2, 39 ketones including aromatic, heteroaryl, and alkyl ketones have been hydrogenated, all affording valuable chiral alcohols with 96.0–99.9% ee. A plausible reaction mechanism was discussed by NMR, HRMS, and DFT, and an activating model involving trihydride was verified.
Topics & Concepts
ChemistryCinchonaIridiumCatalysisAsymmetric hydrogenationReagentLigand (biochemistry)Organic chemistryAlkaloidKetoneAlkylCombinatorial chemistryEnantioselective synthesisBiochemistryReceptorAsymmetric Hydrogenation and CatalysisSurface Chemistry and CatalysisCarbon dioxide utilization in catalysis