Cu(I)-catalyzed intramolecular cyclization of alkynoic acids in aqueous media: a "click side reaction"

J Org Chem. 2007 Dec 21;72(26):10247-50. doi: 10.1021/jo702030e. Epub 2007 Nov 29.

Abstract

Alkynoic acids, in particular, 4-pentynoic acid derivatives, undergo intramolecular cyclizations to enol lactones under reaction conditions typically applied for the Cu(I)-catalyzed cycloaddition of terminal alkynes and azides (click chemistry). Starting from appropriate alkynoic acid derivatives, either enol lactones or 1,2,3-triazole click products can be obtained selectively by Cu(I) catalysis in aqueous media.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Carboxylic Acids / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Cyclization
  • Lactones / chemical synthesis*
  • Lactones / chemistry
  • Molecular Structure
  • Stereoisomerism
  • Water / chemistry

Substances

  • Alkynes
  • Carboxylic Acids
  • Lactones
  • Water
  • Copper