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

Merabet-Khelassi, Mounia;Vriamont, Nicolas;Aribi-Zouioueche, Louisa;Riant, Olivier
(2011) Tetrahedron: Asymmetry — Vol. 22, n° 18-19, p. 1790-1796 (2011)

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Authors
  • Merabet-Khelassi, Mounia
    Author
  • Vriamont, Nicolas
    Author
  • Aribi-Zouioueche, Louisa
    Author
  • Riant, OlivierUCLouvain
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Abstract
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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Merabet-Khelassi, M., Vriamont, N., Aribi-Zouioueche, L., & Riant, O. (2011). Racemization of secondary alcohols catalyzed by ruthenium: Application to chemoenzymatic dynamic resolution. Tetrahedron: Asymmetry, 22(18-19), 1790-1796. https://doi.org/10.1016/j.tetasy.2011.10.007 (Original work published 2011)