Relay Organophotoredox/<i>N</i>-Heterocyclic Carbene Catalysis-Enabled Asymmetric Synthesis of Dibenzoxazepine-Fused Pyrrolidinones
Yaseen Hussain, Deepak Sharma, Tamanna Tamanna, Pankaj Chauhan
Abstract
An unprecedented highly stereoselective synthesis of pyrrolo[1,2- d ][1,4]oxazepin-3(2 H )-ones has been accomplished via photoredox/ N -heterocyclic carbene (NHC) relay catalysis. A wide range of substituted dibenzoxazepines and aryl/hetereoaryl enals were well accommodated under the organic photoredox catalysis-promoted amine oxidation to generate the imines, followed by a NHC-catalyzed [3 + 2] annulation reaction to achieve excellent diastereo- and enantioselectivities of the dibenzoxazepine-fused pyrrolidinones.
Topics & Concepts
ChemistryCarbeneAnnulationCatalysisPyrrolidinonesCombinatorial chemistryAmine gas treatingStereoselectivityArylOrganocatalysisOrganic chemistryEnantioselective synthesisAlkylCatalytic C–H Functionalization MethodsN-Heterocyclic Carbenes in Organic and Inorganic ChemistryCatalytic Cross-Coupling Reactions