Synthesis of enol lactones via Cu(I)-catalyzed intramolecular O-vinylation of carboxylic acids

Org Lett. 2009 Sep 17;11(18):4084-7. doi: 10.1021/ol9015578.

Abstract

With the catalysis of CuI/trans-N,N'-dimethylcyclohexane-1,2-diamine, a number of carboxylic acids underwent efficient intramolecular O-vinylation with vinyl bromides leading to the synthesis of the corresponding five- and six-membered enol lactones. The same catalytic system also led to the efficient cycloisomerization of alkynoic acids.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carboxylic Acids / chemistry*
  • Catalysis
  • Cyclization
  • Diamines / chemistry*
  • Lactones / chemical synthesis*
  • Stereoisomerism*
  • Sulfhydryl Compounds / chemistry
  • Vinyl Compounds / chemistry*

Substances

  • Carboxylic Acids
  • Diamines
  • Lactones
  • Sulfhydryl Compounds
  • Vinyl Compounds
  • vinyl bromide