Synthesis of β-iodo-α-(hydroxyalkyl)acrylates: A convenient and stereoselective reaction

Han Xun Wei, Guigen Li, Joe J. Gao, Paul W. Paré

Research output: Contribution to journalArticle

31 Scopus citations

Abstract

An efficient one-pot, three-component coupling reaction for the synthesis of β-iodo-α-(hydroxyalkyl) acrylates has been developed. As the iodine source as well as the Lewis acid mediator, diethyl aluminium iodide undergoes a Michael-type addition with methyl propynoate to form an active β-iodo allenolate intermediate, which in turn attacks various aldehydes or ketones to afford β-iodo Baylis-Hillman adducts in excellent yields with high Z-selectivity.

Original languageEnglish
Pages (from-to)5677-5680
Number of pages4
JournalTetrahedron Letters
Volume43
Issue number32
DOIs
StatePublished - Aug 5 2002

Keywords

  • Baylis-Hillman adducts
  • Diethyl aluminium iodide
  • Methyl propynoate
  • β-iodo-α-(hydroxyalkyl)acrylates

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