Issue 18, 2010
From the journal:

Organic & Biomolecular Chemistry

Switching from (R)- to (S)-selective chemoenzymatic DKR of amines involving sulfanyl radical-mediated racemization†

Lahssen El Blidi,a   Nicolas Vanthuyne,b   Didier Siri,c   Stéphane Gastaldi,*a   Michèle P. Bertrand*a  and  Gérard Gil*b  

* Corresponding authors

a Equipe Chimie Moléculaire Organique, LCP UMR 6264, Boite 562, Université Paul Cézanne, Faculté des Sciences St Jérôme, Avenue Escadrille Normandie-Niemen, Marseille Cedex 20, (France)
E-mail: michele.bertrand@univ-cezanne.fr

b Laboratoire de Stéréochimie Dynamique et Chiralité, ISM2, UMR 6263, Université Paul Cézanne, Faculté des Sciences St Jérôme, Avenue Escadrille Normandie-Niemen, Marseille Cedex 20, (France)

c Equipe Chimie Théorique et Modélisation Moléculaire, LCP UMR 6264, Université de Provence, Faculté des Sciences St Jérôme, Avenue Escadrille Normandie-Niemen, Marseille Cedex 20, (France)

Abstract

Chemoenzymatic dynamic kinetic resolution (DKR) of amines involving sulfanyl radical-induced racemization happened to be the very first switchable DKR process allowing the synthesis of either (R)- or (S)-amides, in good yield and high enantiomeric excess, depending on the nature of the enzyme; the different steps of the development of (S)-selective DKR are discussed.

Graphical abstract: Switching from (R)- to (S)-selective chemoenzymatic DKR of amines involving sulfanyl radical-mediated racemization

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Article information

DOI
https://doi.org/10.1039/C0OB00054J
Article type
Paper
Submitted
28 Apr 2010
Accepted
29 Jun 2010
First published
27 Jul 2010

Org. Biomol. Chem., 2010,8, 4165-4168

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Switching from (R)- to (S)-selective chemoenzymatic DKR of amines involving sulfanyl radical-mediated racemization

L. El Blidi, N. Vanthuyne, D. Siri, S. Gastaldi, M. P. Bertrand and G. Gil, Org. Biomol. Chem., 2010, 8, 4165 DOI: 10.1039/C0OB00054J

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