Access to dihydropyridinones and spirooxindoles: application of N-heterocyclic carbene-catalyzed [3+3] annulation of enals and oxindole-derived enals with 2-aminoacrylates

Chemical Communications : Chem Comm
Liang-Liang ZhaoJing Qi

Abstract

A strategy for the NHC-catalyzed synthesis of dihydropyridinones and spirooxindoles has been developed via [3+3] annulation reactions of enals or isatin-derived enals with 2-aminoacrylates under oxidative conditions. In this efficient strategy, the 2-aminoacrylates served as nucleophiles. Modifying the standard base switched the carbon-carbon double bond formation from 5,6-positions to 3,4-positions to generate 5,6-dihydropyridinones and 3,4-dihydropyridinones, respectively. Meanwhile, a diverse set of spirooxindole derivatives were also synthesized in good to excellent yields.

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Citations

Nov 9, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Yue LiuJun-Long Li
Feb 23, 2020·Beilstein Journal of Organic Chemistry·Thomas J CogswellRodolfo Marquez
Apr 22, 2020·The Journal of Organic Chemistry·Krzysztof DzieszkowskiZbigniew Rafiński

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