A new entry of copper-catalyzed four-component reaction: facile access to alpha-aryl beta-hydroxy imidates

Org Lett. 2009 Mar 5;11(5):1155-8. doi: 10.1021/ol900023t.

Abstract

Alpha-aryl beta-hydroxy imidates are efficiently obtained by the four-component reaction of ethyl glyoxylates, aryl acetylenes, sulfonyl azides, and alcohols using a copper catalyst. The developed procedure is characterized by high selectivity, mild reaction conditions, a wide substrate scope, and an excellent functional group tolerance. Facile transformations of the obtained sulfonylimidate moiety to other carbonyl groups such as sulfonamides or esters were also demonstrated.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry*
  • Alkynes / chemistry*
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Copper / chemistry*
  • Imidoesters / chemical synthesis*
  • Imidoesters / chemistry
  • Molecular Structure
  • Stereoisomerism
  • Sulfonamides / chemical synthesis
  • Sulfonamides / chemistry

Substances

  • Alcohols
  • Alkynes
  • Imidoesters
  • Sulfonamides
  • Copper