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Bifunctional Brønsted base catalyzed inverse-electron-demand aza-Diels–Alder reactions of saccharin-derived 1-azadienes with azlactones

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Abstract

An enantioselective inverse-electron-demand aza-Diels–Alder reaction of saccharin-derived 1-azadienes and azlactones was developed using a phenylalanine-derived bifunctional Brønsted base-squaramide catalyst, which furnished the chiral tricyclic architectures bearing a quaternary amino acid moiety in high yields with moderate to excellent selectivities. A gram-scale synthesis and further elaboration of the product were also conducted to further demonstrate the synthetic utility of the reaction.

Graphical abstract: Bifunctional Brønsted base catalyzed inverse-electron-demand aza-Diels–Alder reactions of saccharin-derived 1-azadienes with azlactones

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Publication details

The article was received on 12 Mar 2019, accepted on 08 May 2019 and first published on 09 May 2019


Article type: Research Article
DOI: 10.1039/C9QO00357F
Org. Chem. Front., 2019, Advance Article

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    Bifunctional Brønsted base catalyzed inverse-electron-demand aza-Diels–Alder reactions of saccharin-derived 1-azadienes with azlactones

    X. Ren, J. Lin, X. Hu and P. Xu, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO00357F

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