Synthesis of Chiral Diaryl Methanols via RuPHOX‐Ru Catalyzed Asymmetric Hydrogenation
Jiayu Zhou, Jianxun Ye, Yang Zhang, Zhaodi Li, Jingjing Li, Delong Liu, Wanbin Zhang
Abstract
Abstract The RuPHOX‐Ru catalyzed asymmetric hydrogenation of diaryl ketones has been established, providing the corresponding chiral diaryl methanols in up to 99% yield and 99% ee. The protocol could be performed on a gram‐scale with a relatively low catalyst loading (2000 S/C) and the resulting products allow for several useful transformations, in particular for the synthesis of chiral drugs, such as, ( S )‐Orphenadrine and ( S )‐Neobenodine. Deuterium labeling and control experiments revealed that the RuPHOX‐Ru‐catalyzed asymmetric hydrogenation is fully subject to hydrogenation with H 2 as the sole hydrogen source. magnified image
Topics & Concepts
ChemistryAsymmetric hydrogenationCatalysisYield (engineering)Noyori asymmetric hydrogenationCombinatorial chemistryEnantioselective synthesisDeuteriumHydrogenOrganic chemistryPhysicsQuantum mechanicsMetallurgyMaterials scienceAsymmetric Hydrogenation and CatalysisCatalytic C–H Functionalization MethodsCarbon dioxide utilization in catalysis