Organocatalytic Asymmetric Three-Component Povarov Reactions of Anilines and Aldehydes
Jun-Xiang Huang, Ke‐Qiang Hou, Qi-Long Hu, Xueping Chen, Jian Li, Albert S. C. Chan, Xiao‐Feng Xiong
Abstract
We report the first highly enantio- and diastereoselective three-component Povarov reaction between anilines and aldehydes catalyzed by a chiral amine catalyst. A wide variety of substituted tetrahydroquinolines were obtained with moderate to good yields and excellent enantioselectivity and diastereoselectivity (up to 99% ee and >95:5 dr) under the reaction conditions. Furthermore, the reaction intermediates could be efficiently converted to other valuable building blocks.
Topics & Concepts
ChemistryCatalysisComponent (thermodynamics)Amine gas treatingOrganic chemistryReaction conditionsOrganocatalysisCombinatorial chemistryEnantioselective synthesisThermodynamicsPhysicsAsymmetric Synthesis and CatalysisSynthetic Organic Chemistry MethodsOxidative Organic Chemistry Reactions