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CAL-B-Catalyzed Enantioselective Deacetylation of Some Benzylic Acetate Derivatives Via Alcoholysis in Non-aqueous Media

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Abstract

Enantioselective deacetylation of a set of benzylic acetates via alcoholysis catalyzed by Lipase B from Candida antarctica (CAL-B), under mild conditions is described. A systematic study allows to determine the appropriate combination nucleophile/organic solvent and also to explain the influence of these parameters on the enzymatic catalytic reaction. In all cases, (R)-alcohols are obtained with high ee (up to >99 %) at conversion 36 % < C < 48 %, the selectivity reaching E > 500. The enzymatic reactivity is influenced by the hydrophobicity of solvent and the structure/nature of the nucleophile. Furthermore, CAL-B allows enantio-complementary between transesterifications in non-aqueous media: alcoholysis and acetylation.

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Acknowledgments

Algerian Ministry of Higher Education and Scientific Research (MESRS, FNR 2000) and ANDRU (PNR) are gratefully acknowledged for financial support of this work. Prof. Olivier RIANT (IMCN/Louvain Catholic University -UCL- Louvain-La-Neuve, Belgium) is acknowledged for his help and the welcome of Amna ZAÏDI and Mounia MERABET to perform specific analyses.

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Authors and Affiliations

  1. Ecocompatible Asymmetric Catalysis Laboratory (L.C.A.E), Badji Mokhtar Annaba-University, B.P 12, 23000, Annaba, Algeria

    Amna Zaïdi, Mounia Merabet-Khelassi & Louisa Aribi-Zouioueche

Authors
  1. Amna Zaïdi
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  2. Mounia Merabet-Khelassi
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  3. Louisa Aribi-Zouioueche
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Correspondence to Louisa Aribi-Zouioueche.

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Zaïdi, A., Merabet-Khelassi, M. & Aribi-Zouioueche, L. CAL-B-Catalyzed Enantioselective Deacetylation of Some Benzylic Acetate Derivatives Via Alcoholysis in Non-aqueous Media. Catal Lett 145, 1054–1061 (2015). https://doi.org/10.1007/s10562-014-1470-7

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  • DOI: https://doi.org/10.1007/s10562-014-1470-7

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