Racemization of secondary alcohols catalyzed by ruthenium: Application to chemoenzymatic dynamic resolution

In this paper, we have shown that the [RuCl2(p-cymene)] 2 complex associated with simple hemisalen ligands is able to racemize (S)-1-phenylethanol. The influence on the racemization process of the ligand's structure as well as the nature of a co-catalyst have been evaluated and optimized. This...

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Bibliographic Details
Published in:Tetrahedron: Asymmetry
Main Authors: Merabet-Khelassi, Mounia, Vriamont, Nicolas, Aribi-Zouioueche, Louisa, Riant, Olivier
Other Authors: UCL - SST/IMCN/MOST - Molecules, Solids and Reactivity
Format: Article in Journal/Newspaper
Language:English
Published: Pergamon 2011
Subjects:
1 phenylethanol
Acetic acid ethyl ester
Catalysis
Catalyst
Chemical structure
Enantioselectivity
Priority journal
Racemization
Reaction analysis
Alcohol derivative
Benzyl derivative
Ligand
Ruthenium
Triacylglycerol lipase
Article
Biotransformation
Candida antarctica
Antarc*
Antarctica
Online Access:http://hdl.handle.net/2078.1/107737
https://doi.org/10.1016/j.tetasy.2011.10.007
Description
Summary:In this paper, we have shown that the [RuCl2(p-cymene)] 2 complex associated with simple hemisalen ligands is able to racemize (S)-1-phenylethanol. The influence on the racemization process of the ligand's structure as well as the nature of a co-catalyst have been evaluated and optimized. This [RuCl2(p-cymene)]2/Ligand/TEMPO racemization system was then associated with the Candida Antarctica B lipase in order to carry out dynamic kinetic resolution experiments on rac-phenylethanol. This led us to identify the best conditions for effective DKR, which was then applied to various secondary benzylic and aliphatic alcohols. It was thus possible to obtain (R)-1-cyclohexylethyl acetate from rac-1-cyclohexylethanol in quantitative conversion and with high enantioselectivity (98%). © 2011 Elsevier Ltd. All rights reserved.

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