Herein, we present a sustainable photochemical approach for the synthesis of 3,4-dihydroquinolin-2-(1H)-ones via TBADT (hydrogen-atom transfer) catalyst-mediated radical cascade cyclization of alkyl (E)-3-(2-methacrylamidoaryl)acrylates with cycloalkanes. Significantly, the products were obtained with a high syn stereoselectivity between the ester group and the incoming radical source. This strategy enables the diversification of functionalized alkyl (E)-3-(2-methacrylamidoaryl)acrylate with a drug. This transformation operates under mild reaction conditions and enables dual C-C bond formation. Notably, scale-up reactions and mechanistic investigations were performed.
Rao et al. (Fri,) studied this question.