Carbene-Catalyzed Direct O-Functionalization of Ketone: Atroposelective Access to Non-<i>C</i><sub>2</sub>-Symmetric Binaphthyls
Bivas Mondal, Hang Chen, Rakesh Maiti, Hongling Wang, Hui Cai, Chengli Mou, Hao Lin, Huifang Chai, Yonggui Robin
Abstract
Disclosed here is NHC-catalyzed direct intermolecular trapping of the ketone oxygen atom with the acyl azolium intermediate. The overall reaction is a dynamic kinetic resolution process that converts ketone to the corresponding enol ester with well-controlled axial chirality. Our reaction eventually affords non- C 2 -symmetric binaphthyl derivatives with important applications, such as in the area of asymmetric catalysis.
Topics & Concepts
ChemistryKetoneCatalysisKinetic resolutionIntermolecular forceCarbeneSurface modificationEnolAxial chiralityChirality (physics)Enantioselective synthesisStereochemistryCombinatorial chemistryMoleculeOrganic chemistryPhysical chemistryQuarkQuantum mechanicsNambu–Jona-Lasinio modelPhysicsChiral symmetry breakingAxial and Atropisomeric Chirality SynthesisSynthetic Organic Chemistry MethodsN-Heterocyclic Carbenes in Organic and Inorganic Chemistry