Divergent Synthesis of <i>β</i>‐Hydroxy Amides (Esters) and <i>γ</i>‐Amino Alcohols via Ir/<i>f</i>‐Diaphos Catalyzed Asymmetric Hydrogenation
Xianghua Zhao, Zehui Yang, Yuqi Cheng, An Huang, Fangyuan Hu, Fei Ling, Weihui Zhong
Abstract
Abstract The iridium/ f ‐diaphos L2 or L9 catalyzed asymmetric hydrogenation of β ‐aryl β ‐keto amides (esters), and β ‐amino ketones to afford two enantiomers of the desired chiral alcohols was realized with 90%‐99% yield and 73%‐99% ee . This protocol could be easily conducted on gram scale in the presence of low catalyst loading (up to 9900 TON). Moreover, the hydrogenated products are versatile building blocks for a variety of biologically active molecules and drugs, such as Fluoxetine, Dapoxetine and so on. magnified image
Topics & Concepts
ChemistryCatalysisAsymmetric hydrogenationEnantiomerYield (engineering)IridiumEnantioselective synthesisEnantiomeric excessArylOrganic chemistryAmino estersAmino acidCombinatorial chemistryMoleculeAlkylBiochemistryMaterials scienceMetallurgyAsymmetric Hydrogenation and CatalysisChemical Synthesis and AnalysisAdvanced Synthetic Organic Chemistry