Issue 47, 2020

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

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

Supplementary files

Article information

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

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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