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

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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.

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

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Publication details

The article was received on 11 Apr 2017, accepted on 08 May 2017 and first published on 10 May 2017


Article type: Communication
DOI: 10.1039/C7CC02753B
Citation: Chem. Commun., 2017, Advance Article
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    Access to dihydropyridinones and spirooxindoles: application of N-heterocyclic carbene-catalyzed [3+3] annulation of enals and oxindole-derived enals with 2-aminoacrylates

    L. Zhao, X. Li, L. Cao, R. Zhang, X. Shi and J. Qi, Chem. Commun., 2017, Advance Article , DOI: 10.1039/C7CC02753B

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