Catalysis Letters

, Volume 148, Issue 6, pp 1750–1757 | Cite as

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

  • Sebastián M. Ardanaz
  • Ana J. Velez Rueda
  • Gustavo Parisi
  • Adolfo M. Iribarren
  • Luis E. Iglesias
Article
  • 32 Downloads

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.

Graphical Abstract

Keywords

Bovine serum albumin Catalytic promiscuity Cross aldol condensation Enones 

Notes

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.

Supplementary material

10562_2018_2386_MOESM1_ESM.pdf (187 kb)
Supplementary material 1 (PDF 186 KB)

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Sebastián M. Ardanaz
    • 1
  • Ana J. Velez Rueda
    • 2
  • Gustavo Parisi
    • 2
  • Adolfo M. Iribarren
    • 1
  • Luis E. Iglesias
    • 1
  1. 1.Laboratory of Biocatalysis and Biotransformation, Department of Science and TechnologyNational University of QuilmesBernalArgentina
  2. 2.Structural Bioinformatics Group, Department of Science and TechnologyNational University of QuilmesBernalArgentina

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