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 avr. 2020
Accepted
28 avr. 2020
First published
28 avr. 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

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements