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Issue 18, 2010
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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 
Author affiliations

* 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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Publication details

The article was received on 28 Apr 2010, accepted on 29 Jun 2010 and first published on 27 Jul 2010


Article type: Paper
DOI: 10.1039/C0OB00054J
Citation: 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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