Asymmetric Aminative Dearomatization of 2-Naphthols via Non-covalent N-Heterocyclic Carbene Catalysis
Ujjwal Maji, Bhaskar Mondal, Joyram Guin
Abstract
Herein, successful utilization of non-covalent N-heterocyclic carbene (NHC) catalysis toward asymmetric aminative dearomatization of naphthols is presented. The NHC-catalyzed process offers enantioselective synthesis of cyclic enones possessing a nitrogen-containing α-quaternary stereocenter. The reaction applies to various functionalized substrates including acid-labile groups and is shown to be scalable. Substrate activation via an O-H···NHC hydrogen-bonding interaction is suggested based on the results obtained in mechanistic studies.
Topics & Concepts
ChemistryCarbeneStereocenterEnantioselective synthesisCatalysisOrganocatalysisCovalent bondSubstrate (aquarium)Combinatorial chemistryHydrogen bondStereochemistryOrganic chemistryMoleculeGeologyOceanographyN-Heterocyclic Carbenes in Organic and Inorganic ChemistrySynthetic Organic Chemistry MethodsCatalytic C–H Functionalization Methods