Issue 11, 2011
From the journal:

Green Chemistry

Laccase-catalyzed stereoselective oxidative ring opening of 2,5-dialkylfurans into 2-ene-1,4-diones using air as an oxidant†

Chimène Asta,a   Jürgen Conrad,a   Sabine Mikaa  and  Uwe Beifuss,†*a  

* Corresponding authors

a Bioorganische Chemie, Institut für Chemie, Universität Hohenheim, Garbenstr. 30, Stuttgart, Germany
E-mail: ubeifuss@uni-hohenheim.de
Fax: (+49) 711459 22951
Tel: (+49) 711 459 22171

Abstract

The laccase-catalyzed ring opening of 2,5-dimethylfuran using air as an oxidant stereoselectively yields (Z)- or (E)-3-hexene-2,5-dione depending on the mediator employed: with TEMPO the (Z)-3-hexene-2,5-dione is formed, while a combination of TEMPO and violuric acid gives (E)-3-hexene-2,5-dione. The (Z)-selective ring cleavage was extended to a variety of symmetrical and unsymmetrical 2,5-dialkylfurans.

Graphical abstract: Laccase-catalyzed stereoselective oxidative ring opening of 2,5-dialkylfurans into 2-ene-1,4-diones using air as an oxidant

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Article information

DOI
https://doi.org/10.1039/C1GC15810D
Article type
Communication
Submitted
07 Jul 2011
Accepted
03 Aug 2011
First published
13 Sep 2011

Green Chem., 2011,13, 3066-3069

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Laccase-catalyzed stereoselective oxidative ring opening of 2,5-dialkylfurans into 2-ene-1,4-diones using air as an oxidant

C. Asta, J. Conrad, S. Mika and U. Beifuss,†, Green Chem., 2011, 13, 3066 DOI: 10.1039/C1GC15810D

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