The synthesis of chiral isotetronic acids with amphiphilic imidazole/pyrrolidine catalysts assembled in oil-in-water emulsion droplets

Angew Chem Int Ed Engl. 2012 Dec 21;51(52):13159-62. doi: 10.1002/anie.201206438. Epub 2012 Nov 14.

Abstract

Drop it! A highly enantioselective catalytic cascade reaction of α-ketoacids and aldehydes is achieved using the title catalyst and water as the solvent. Fluorescence imaging shows that the catalyst is mainly distributed on the surface of emulsion droplets. Optically active isotetronic acids can be obtained with this method and the emulsion droplets are responsible for the high reactivity and enantioselectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry
  • Catalysis
  • Emulsions / chemistry
  • Flavoring Agents / chemical synthesis
  • Flavoring Agents / chemistry
  • Furans / chemical synthesis
  • Furans / chemistry*
  • Imidazoles / chemistry*
  • Micelles
  • Microscopy, Fluorescence
  • Oils / chemistry*
  • Pyrrolidines / chemistry*
  • Stereoisomerism
  • Water / chemistry*

Substances

  • Aldehydes
  • Emulsions
  • Flavoring Agents
  • Furans
  • Imidazoles
  • Micelles
  • Oils
  • Pyrrolidines
  • Water
  • imidazole
  • pyrrolidine
  • tetronic acid