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Issue 1, 2019
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Asymmetric construction of dihydrobenzofuran-2,5-dione derivatives via desymmetrization of p-quinols with azlactones

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Abstract

The desymmetrization of p-quinols through a chiral bisguanidinium hemisalt catalyzed enantioselective Michael addition/lactonization cascade reaction with azlactones was reported. 3-Amino-benzofuran-2,5-diones containing a chiral amino acid residue were achieved with up to 99% ee and >19 : 1 dr. An exploration of the structure of the catalyst bisguanidinium was undertaken, revealing a bifunctional catalytic model.

Graphical abstract: Asymmetric construction of dihydrobenzofuran-2,5-dione derivatives via desymmetrization of p-quinols with azlactones

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Publication details

The article was received on 12 Nov 2018, accepted on 15 Nov 2018 and first published on 04 Dec 2018


Article type: Communication
DOI: 10.1039/C8CC08985J
Chem. Commun., 2019,55, 87-90

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    Asymmetric construction of dihydrobenzofuran-2,5-dione derivatives via desymmetrization of p-quinols with azlactones

    L. Xie, S. Dong, Q. Zhang, X. Feng and X. Liu, Chem. Commun., 2019, 55, 87
    DOI: 10.1039/C8CC08985J

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