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Light-Driven Enantioselective Carbene-Catalyzed Radical-Radical Coupling.


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.

SUBMITTER: Byun S 

PROVIDER: S-EPMC10841513 | biostudies-literature | 2023 Dec

REPOSITORIES: biostudies-literature

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Light-Driven Enantioselective Carbene-Catalyzed Radical-Radical Coupling.

Byun Seunghwan S   Hwang Meemie U MU   Wise Henry R HR   Bay Anna V AV   Cheong Paul H-Y PH   Scheidt Karl A KA  

Angewandte Chemie (International ed. in English) 20231106 49


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 sp<sup>3</sup> -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 pharmaceu  ...[more]

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