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A Mild Procedure for Enone Preparation Catalysed by Bovine Serum Albumin in a Green and Easily Available Medium

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Abstract

A simple and mild procedure to obtain α,β-unsaturated ketones from acetone and a set of benzaldehydes is described. The approach applies bovine serum albumin (BSA) catalysis and water or ethanol, this mild reaction medium contrasting with the strong reaction conditions of the classic aldol condensation. Except for the assayed nitrobenzaldehydes, high enone yields (88–97%) were attained. In addition to its mildness, further advantages of this procedure are the use of a green catalyst exhibiting an efficient reuse and the use of eco-friendly and cheap solvents. In order to gain a deeper understanding of the involved catalytic mechanism, computational experiments on BSA structural analysis and molecular docking were carried out.

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Acknowledgements

The authors acknowledge UNQ and ANPCyT, Argentina (PICT 2013-0232, LEI) for financial support. GP, AMI and LEI are members of the Scientific Research Career of CONICET (Argentina); SMI is research fellow of CONICET and AJVL, research fellow of ANPCyT.

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Authors and Affiliations

  1. Laboratory of Biocatalysis and Biotransformation, Department of Science and Technology, National University of Quilmes, Roque Sáenz Peña 352, 1876, Bernal, Provincia De Buenos Aires, Argentina

    Sebastián M. Ardanaz, Adolfo M. Iribarren & Luis E. Iglesias

  2. Structural Bioinformatics Group, Department of Science and Technology, National University of Quilmes, Roque Sáenz Peña 352, 1876, Bernal, Provincia De Buenos Aires, Argentina

    Ana J. Velez Rueda & Gustavo Parisi

Authors
  1. Sebastián M. Ardanaz
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  2. Ana J. Velez Rueda
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  3. Gustavo Parisi
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  4. Adolfo M. Iribarren
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  5. Luis E. Iglesias
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Corresponding author

Correspondence to Luis E. Iglesias.

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Ardanaz, S.M., Velez Rueda, A.J., Parisi, G. et al. A Mild Procedure for Enone Preparation Catalysed by Bovine Serum Albumin in a Green and Easily Available Medium. Catal Lett 148, 1750–1757 (2018). https://doi.org/10.1007/s10562-018-2386-4

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  • DOI: https://doi.org/10.1007/s10562-018-2386-4

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