Boron-catalyzed direct aldol reactions of pyruvic acids

Org Lett. 2009 Dec 3;11(23):5486-9. doi: 10.1021/ol902322r.

Abstract

Interactions between pyruvic acids and diphenylborinic acid form the basis of an efficient, direct, boron-catalyzed aldol reaction that takes place in water at room temperature with low catalyst loadings. Both boronic and borinic acids function as catalysts, with the latter demonstrating particularly high activity. A wide range of aldehydes, including enolizable species, may be employed, delivering useful isotetronic acid derivatives in high yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Borinic Acids / chemistry
  • Boron Compounds / chemistry*
  • Catalysis
  • Cyclization
  • Molecular Structure
  • Pyruvic Acid / analogs & derivatives*
  • Pyruvic Acid / chemistry*

Substances

  • Borinic Acids
  • Boron Compounds
  • Pyruvic Acid