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

Erika Tassano; Kemal Merusic; Isa Buljubasic; Olivia Laggner; Tamara Reiter; Andreas Vogel; Mélanie Hall

doi:10.1039/D0CC02509G

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

Erika Tassano,

^a Kemal Merusic,

^a Isa Buljubasic,^a Olivia Laggner,^a Tamara Reiter,^a Andreas Vogel^b and Mélanie Hall

*^a

Author affiliations

* 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.

This article is part of the themed collections: Chemical Communications HOT Articles and Organic Synthesis

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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

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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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Chemical Communications

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

Abstract

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

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