Issue 5, 2019

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
11 Dec. 2018
Accepted
12 Janv. 2019
First published
17 Janv. 2019

Org. Chem. Front., 2019,6, 579-583

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, 6, 579 DOI: 10.1039/C8QO01335G

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