Facile synthesis of alpha-substituted acrylate esters

J Org Chem. 2002 Oct 18;67(21):7365-8. doi: 10.1021/jo026101s.

Abstract

Treatment of 5-monosubstituted Meldrum's acids with dimethylmethyleneimmonium iodide (Eschenmoser's iodide salt) in methanol gives alpha-substituted acrylate methyl esters in good yields. Easy access to 5-monosubstituted Meldrum's acids allowed us to synthesize a wide variety of alpha-substituted acrylate methyl esters. The reaction conditions are mild and tolerate many functional groups commonly used in organic synthesis; thus, this new method has potential as an alternative to conventional preparative methods for alpha-substituted acrylate esters.

MeSH terms

  • Acrylates / chemical synthesis*
  • Carboxylic Acids*
  • Enzyme Inhibitors / chemical synthesis
  • Esters / chemical synthesis*
  • Indicators and Reagents
  • Metalloendopeptidases / antagonists & inhibitors
  • Structure-Activity Relationship

Substances

  • Acrylates
  • Carboxylic Acids
  • Enzyme Inhibitors
  • Esters
  • Indicators and Reagents
  • Metalloendopeptidases