Issue 1, 2019

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

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

Supplementary files

Article information

Article type
Communication
Submitted
12 Nov 2018
Accepted
15 Nov 2018
First published
04 Dec 2018

Chem. Commun., 2019,55, 87-90

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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