A Combination of Visible-Light Organophotoredox Catalysis and Asymmetric Organocatalysis for the Enantioselective Mannich Reaction of Dihydroquinoxalinones with Ketones

[EN] An enantioselective photooxidative Mannich reaction of dihydroquinoxalinones with ketones by the merger of organophotoredox and asymmetric organocatalysis is described. This protocol features very mild reaction conditions using simple and cheap catalysts (Eosin Y and (S)-Proline) for the synthesis of chiral quinoxaline derivatives with good to high yields (up to 94%) and excellent enantioselectivities (up to 99% ee).Financial support from the Agencia Estatal de Investigation (AEI, Spanish Government) and Fondo Europeo de Desarrollo Regional (FEDER, European Union) (CTQ2017-84900-P) is acknowledged. J.R.-B. thanks the Ministerio de Ciencia, Innovacion y Universidades for an FPU predoctoral contract, and C.V. thanks the Agencia Estatal de Investigacion (AEI, Spanish Government) for an RyC contract (RYC-2016-20187).Rostoll-Berenguer, J.; Blay, G.; Muñoz Roca, MDC.; Pedro, J.; Vila, C. (2019). A Combination of Visible-Light Organophotoredox Catalysis and Asymmetric Organocatalysis for the Enantioselective Mannich Reaction of Dihydroquinoxalinones with Ketones. Organic Letters. 21(15):6011-6015. https://doi.org/10.1021/acs.orglett.9b0215760116015211