Synthesis and recovery of pyridine- and piperidine-based camphorsulfonamide organocatalysts used for Michael addition reaction

  • Péter Kisszékelyi Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, H-1521 Budapest, P.O. Box 91, Hungary https://orcid.org/0000-0002-9529-0674
  • Sándor Nagy Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, H-1521 Budapest, P.O. Box 91, Hungary https://orcid.org/0000-0001-6251-5382
  • Blanka Tóth Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, H-1521 Budapest, P.O. Box 91, Hungary
  • Bálint Zeller Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, H-1521 Budapest, P.O. Box 91, Hungary
  • László Hegedűs Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, H-1521 Budapest, P.O. Box 91, Hungary http://orcid.org/0000-0002-7980-0443
  • Béla Mátravölgyi Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, H-1521 Budapest, P.O. Box 91, Hungary
  • Alajos Grün Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, H-1521 Budapest, P.O. Box 91, Hungary
  • Tamás Németh nstitute of Organic Chemistry, Research Centre for Natural Sciences, Hungarian Academy of Sciences, H-1519 Budapest, P.O. Box 286, Hungary
  • Péter Huszthy Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, H-1521 Budapest, P.O. Box 91, Hungary https://orcid.org/0000-0001-7305-3312
  • József Kupai Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, H-1521 Budapest, P.O. Box 91, Hungary http://orcid.org/0000-0002-4212-4517

Abstract

Two new pyridine-based asymmetric bifunctional organocatalysts containing one or two camphorsulfonamide units were synthesized. Asymmetric Michael addition of pentane-2,4-dione to β-nitrostyrene was catalyzed by these organocatalysts. During our experiments, influence of the solvent and temperature on the yield and enantioselectivity was studied. Using monocamphorsulfonamide derivative the S enantiomer of the corresponding Michael adduct was gained with moderate yield (up to 51 %) and low enantiomeric excess (up to 18 %). Organic solvent nanofiltration was successfully applied for the recovery of these organocatalysts. Furthermore, pyridine camphorsulfonamide was reduced to its piperidine derivative. Using piperidine monosulfonamide derivative racemic Michael adduct was obtained with excellent yield (up to 89 %). Beside its organocatalytic relevance, piperidine monosulfonamide derivative may also possess biological activity.

Keywords: organocatalyst, asymmetric synthesis, camphorsulfonamide, catalyst recovery, Michael addition
Published online
2018-10-31
How to Cite
Kisszékelyi, P., Nagy, S., Tóth, B., Zeller, B., Hegedűs, L., Mátravölgyi, B., Grün, A., Németh, T., Huszthy, P. and Kupai, J. (2018) “Synthesis and recovery of pyridine- and piperidine-based camphorsulfonamide organocatalysts used for Michael addition reaction”, Periodica Polytechnica Chemical Engineering, 62(4), pp. 489–496. doi: https://doi.org/10.3311/PPch.12719.
Section
Articles