Stereoselective aldol coupling of α,β-acetylenic ketones promoted by MgI2

Han Xun Wei, Jiali Hu, David W. Purkiss, Paul W. Paré

Research output: Contribution to journalArticle

34 Scopus citations

Abstract

A highly stereoselective synthesis of (Z)-β-iodovinyl ketone has been achieved with the tandem formation of C-C and C-I bonds in a three-component reaction. This new catalysis utilizes MgI2 as a Lewis acid as well as an iodine source for a Michael-type addition. α,β-Acetylenic ketone is initially converted to an active β-iodo allenolate intermediate and then can be attacked by a variety of aldehydes to afford Z-selective Baylis-Hillman adducts in excellent yields.

Original languageEnglish
Pages (from-to)949-952
Number of pages4
JournalTetrahedron Letters
Volume44
Issue number5
DOIs
StatePublished - Jan 27 2003

Keywords

  • (Z)-β-iodovinyl ketone
  • Baylis-Hillman adducts
  • Magnesium iodide
  • α,β-acetylenic ketones

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