Asymmetric Michael reactions catalyzed by a highly efficient and recyclable quaternary ammonium ionic liquid-supported organocatalyst in aqueous media

Org Biomol Chem. 2013 Mar 21;11(11):1801-4. doi: 10.1039/c3ob27398a. Epub 2013 Feb 4.

Abstract

A novel ionic liquid-support organocatalyst, which contains the quaternary ammonium ion moiety, was recently developed and successfully applied to the asymmetric Michael reaction in the presence of a newly developed ionic liquid-supported (ILS) benzoic acid as co-catalyst. For the reactions studied, in which various aldehydes and nitroolefins were examined, excellent diastereo- and enantioselectivities were obtained with low catalyst loading. Also, the catalyst could be recycled for ten times without significant loss of enantioselectivity.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Aldehydes / chemistry
  • Alkenes / chemistry
  • Benzoic Acid / chemistry
  • Catalysis
  • Ionic Liquids / chemistry*
  • Molecular Structure
  • Nitro Compounds / chemical synthesis
  • Nitro Compounds / chemistry
  • Quaternary Ammonium Compounds / chemistry*
  • Stereoisomerism
  • Water / chemistry

Substances

  • Aldehydes
  • Alkenes
  • Ionic Liquids
  • Nitro Compounds
  • Quaternary Ammonium Compounds
  • Water
  • Benzoic Acid