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Enantioselective synthesis of 3-amino-hydrobenzofuran-2,5-diones via Cu(I)-catalyzed intramolecular conjugate addition of imino esters

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Abstract

A highly enantioselective intramolecular conjugate addition of imino esters was presented. By employing cyclohexadienone-tethered imino esters, enantioenriched 3-amino-hydrobenzofuran-2,5-dione skeletons bearing three contiguous stereocenters were synthesized via the desymmetrization of prochiral cyclohexadienones. Notably, bicyclic cyclohexenones bearing up to three vicinal quaternary stereocenters could be constructed in a single step by this strategy.

Graphical abstract: Enantioselective synthesis of 3-amino-hydrobenzofuran-2,5-diones via Cu(i)-catalyzed intramolecular conjugate addition of imino esters

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Publication details

The article was received on 11 Dec 2018, accepted on 12 Jan 2019 and first published on 17 Jan 2019


Article type: Research Article
DOI: 10.1039/C8QO01335G
Citation: Org. Chem. Front., 2019, Advance Article

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    Enantioselective synthesis of 3-amino-hydrobenzofuran-2,5-diones via Cu(I)-catalyzed intramolecular conjugate addition of imino esters

    W. Yang, Z. Sun, J. Zhang, Z. Li and W. Deng, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C8QO01335G

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