Monatshefte für Chemie - Chemical Monthly

, Volume 138, Issue 11, pp 1181–1186

Stereoselective Michael Addition of Carbonyl Compounds to (E)-β-Nitrostyrene Catalysed by N-Toluensulfonyl-l-proline Amide in Ionic Liquids

  • Mária Mečiarová
  • Katarína Hubinská
  • Štefan Toma
  • Burkhard Koch
  • Albrecht Berkessel
Article

DOI: 10.1007/s00706-007-0732-0

Cite this article as:
Mečiarová, M., Hubinská, K., Toma, Š. et al. Monatsh. Chem. (2007) 138: 1181. doi:10.1007/s00706-007-0732-0

Summary.

N-Toluensulfonyl-l-prolin amide was tested as catalyst in the enantioselective Michael addition of carbonyl compounds to (E)-β-nitrostyrene in nine ionic liquids under different reaction conditions. The reaction rates and enantioselectivities were strongly dependent on the ionic liquids. Change of enantioselectivity was observed too and it is attributed to both the cation and the anion of ionic liquid. The best yields (up to 98%) and enantioselectivity (70% ee) of product were obtained in a basic ionic liquid [bmim]BF4 at room temperature.

Keywords. Ionic liquids; Michael addition; Enantioselectivity; Organocatalysis.

Copyright information

© Springer-Verlag 2007

Authors and Affiliations

  • Mária Mečiarová
    • 1
  • Katarína Hubinská
    • 1
  • Štefan Toma
    • 1
  • Burkhard Koch
    • 2
  • Albrecht Berkessel
    • 2
  1. 1.Department of Organic Chemistry, Faculty of Natural SciencesComenius UniversityBratislavaSlovak Republic
  2. 2.Institut für Organische Chemie der Universität zu KölnKölnGermany