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  • Title: Light-Driven Enantioselective Carbene-Catalyzed Radical-Radical Coupling.
    Author: Byun S, Hwang MU, Wise HR, Bay AV, Cheong PH, Scheidt KA.
    Journal: Angew Chem Int Ed Engl; 2023 Dec 04; 62(49):e202312829. PubMed ID: 37845183.
    Abstract:
    An enantioselective carbene-catalyzed radical-radical coupling of acyl imidazoles and racemic Hantzsch esters is disclosed. This method involves the coupling of an N-heterocyclic carbene-derived ketyl radical and a secondary sp3 -carbon radical and allows access to chiral α-aryl aliphatic ketones in moderate-to-good yields and enantioselectivities without any competitive epimerization. The utility of this protocol is highlighted by the late-stage functionalization of various pharmaceutical compounds and is further demonstrated by the transformation of the enantioenriched products to biologically relevant molecules. Computational investigations reveal the N-heterocyclic carbene controls the double-facial selectivity of the ketyl radical and the alkyl radicals, respectively.
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