Issue 47, 2020
From the journal:

Chemical Communications

Regioselective biocatalytic self-sufficient Tishchenko-type reaction via formal intramolecular hydride transfer†

Erika Tassano, ORCID logo a   Kemal Merusic, ORCID logo a   Isa Buljubasic,a   Olivia Laggner,a   Tamara Reiter,a   Andreas Vogelb  and  Mélanie Hall ORCID logo *a  

* Corresponding authors

a Department of Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz, Austria
E-mail: melanie.hall@uni-graz.at

b c-LEcta GmbH, Perlickstrasse 5, 04103 Leipzig, Germany

Abstract

A self-sufficient nicotinamide-dependent intramolecular bio-Tishchenko-type reaction was developed. The reaction is catalyzed by alcohol dehydrogenases and proceeds through formal intramolecular hydride transfer on dialdehydes to deliver lactones. Regioselectivity on [1,1′-biphenyl]-2,2′-dicarbaldehyde substrates could be controlled via the electronic properties of the substituents. Preparative scale synthesis provided access to substituted dibenzo[c,e]oxepin-5(7H)-ones.

Graphical abstract: Regioselective biocatalytic self-sufficient Tishchenko-type reaction via formal intramolecular hydride transfer

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Article information

DOI
https://doi.org/10.1039/D0CC02509G
Article type
Communication
Submitted
09 apr 2020
Accepted
28 apr 2020
First published
28 apr 2020
This article is Open Access
Creative Commons BY-NC license

Chem. Commun., 2020,56, 6340-6343

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Regioselective biocatalytic self-sufficient Tishchenko-type reaction via formal intramolecular hydride transfer

E. Tassano, K. Merusic, I. Buljubasic, O. Laggner, T. Reiter, A. Vogel and M. Hall, Chem. Commun., 2020, 56, 6340 DOI: 10.1039/D0CC02509G

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