Overcoming the limitations of the Morita-Baylis-Hillman reaction: a rapid and general synthesis of alpha-alkenyl-beta'-hydroxy thioesters

Org Lett. 2008 Nov 6;10(21):4819-22. doi: 10.1021/ol801896q. Epub 2008 Oct 10.

Abstract

Acryloyl chlorides, aldehydes, and PhSLi undergo a direct aldol cascade sequence in the presence of MgBr2 x OEt2 via in situ derived thioester enolates, which is followed by oxidative elimination to give alpha-alkenyl-beta'-hydroxy thioesters. Overall, the procedure is rapid, efficient, and generally applicable, even to beta-substituted acryloyl chlorides, thus providing an alternative to the Morita-Baylis-Hillman reaction with substantially greater synthetic scope and utility.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry
  • Alkenes / chemistry*
  • Esters / chemistry*
  • Hydroxylation
  • Molecular Structure
  • Oxidation-Reduction
  • Sulfhydryl Compounds / chemical synthesis*
  • Sulfhydryl Compounds / chemistry
  • Time Factors

Substances

  • Aldehydes
  • Alkenes
  • Esters
  • Sulfhydryl Compounds
  • 3-hydroxybutanal