Iridium-Catalyzed Asymmetric Hydrogenation of Simple Ketones with Tridentate PNN Ligands Bearing Unsymmetrical Vicinal Diamines
Lei Zhang, Chengyu Liu, Maolin Sun, Chaoming Liang, Liming Cao, Xiantong Yao, Yueyue Ma, Ruihua Cheng, Jinxing Ye
Abstract
An iridium catalytic system with a ferrocene-based phosphine ligand bearing a modular and tunable unsymmetrical vicinal diamine scaffold was developed for the asymmetric hydrogenation of aryl ketones. This approach provided a powerful tool for the enantioselective synthesis of diverse chiral alcohols with excellent reactivity and enantioselectivity (up to 99% yield, up to 99% ee, and up to 50,000 turnover number). The substituents and chirality of unsymmetrical diamines in ligands played an important role in the satisfactory results.
Topics & Concepts
VicinalEnantioselective synthesisAsymmetric hydrogenationChemistryPhosphineDiamineCatalysisFerroceneLigand (biochemistry)Yield (engineering)IridiumArylReactivity (psychology)Combinatorial chemistryStereochemistryOrganic chemistryMaterials scienceAlkylPathologyElectrochemistryReceptorAlternative medicineElectrodePhysical chemistryBiochemistryMetallurgyMedicineAsymmetric Hydrogenation and CatalysisAdvanced Synthetic Organic ChemistrySurface Chemistry and Catalysis