Regioselective biocatalytic self-sufficient Tishchenko-type reaction via formal intramolecular hydride transfer. Issue 47 (11th May 2020)

• Record Type: Journal Article
• Authors: Tassano, Erika; Merusic, Kemal; Buljubasic, Isa; Laggner, Olivia; Reiter, Tamara; Vogel, Andreas; Hall, Mélanie
• Is Part Of: Chemical communications. Volume 56:Issue 47(2020)
• Page Start: 6340
• Page End: 6343
• Publication Date: 2020-05-11
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d0cc02509g
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : Alcohol dehydrogenases catalyze the regioselective lactonization of dialdehydes via a bio-Tishchenko-like reaction. The nicotinamide-dependent self-sufficient reduction–oxidation sequence proceeds through a formal intramolecular hydride shift. 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(7 H )-ones.