Dynamic Kinetic Resolution of α-Trifluoromethyl Hemiaminals without α-Hydrogen via NHC-Catalyzed <i>O</i>-Acylation
Yuan‐Yuan Gao, Chunlin Zhang, Lei Dai, You-Feng Han, Song Ye
Abstract
Following the well-recognized dynamic kinetic resolution (DKR) of hemiaminals with α-hydrogen under lipase and chiral DMAP catalysis, the unprecedented DKR of hemiaminals without α-hydrogen was developed via N-heterocyclic carbene catalyzed O-acylation of 3-hydroxy-3-trifluoromethylbenzosultams. The racemic hemiaminals without α-hydrogen were effectively racemized and differentiated by chiral NHCs under basic conditions. The resulting esters were obtained in high yields with good to high enantioselectivities.
Topics & Concepts
ChemistryKinetic resolutionAcylationCatalysisTrifluoromethylOrganic chemistryCombinatorial chemistryEnantioselective synthesisAlkylN-Heterocyclic Carbenes in Organic and Inorganic ChemistryCarbon dioxide utilization in catalysisFluorine in Organic Chemistry