Asymmetric Synthesis of Hydroquinolines with α,α‐Disubstitution through Organocatalyzed Kinetic Resolution
Yunrong Chen, Chaofan Zhu, Zheng Guo, Wei Liu, Xiaoyu Yang
Abstract
The first kinetic resolution of hydroquinoline derivatives with α,α-disubstitution has been achieved through asymmetric remote aminations with azodicarboxylates enabled by chiral phosphoric acid catalysis. Mechanistic studies suggest a monomeric catalyst pathway proceeding through rate- and enantio-determining electrophilic attack promoted by a network of attractive non-covalent interactions between the substrate and catalyst. Facile subsequent removal and transformations of the newly introduced hydrazine moiety enable these protocols to serve as powerful tools for asymmetric synthesis of N-heterocycles with α,α-disubstitution.
Topics & Concepts
ChemistryKinetic resolutionElectrophileMoietySubstrate (aquarium)CatalysisEnantioselective synthesisCombinatorial chemistryOrganocatalysisPhosphoric acidOrganic chemistryOceanographyGeologyAsymmetric Hydrogenation and CatalysisAsymmetric Synthesis and CatalysisSynthesis and Catalytic Reactions