Z/E stereoselective synthesis of β-bromo Baylis-Hillman ketones using MgBr 2 as promoter via a one-pot three-component reaction

Han Xun Wei, Richard L. Jasoni, Jiali Hu, Guigen Li, Paul W. Paré

Research output: Contribution to journalArticlepeer-review

24 Scopus citations

Abstract

The first time steroselective synthesis of (Z)-β-bromo Baylis-Hillman ketones has been achieved using a one-pot three-component reaction. The new system uses MgBr 2 as both the Lewis acidic promoter and the bromine source for the Michael-type addition with α,β-acetylenic ketones to form an active β-bromo allenolate intermediate, which in turn attacks various aldehydes to afford β-bromo Baylis-Hillman adducts in good yields and Z-selectivity. Graphical Abstract

Original languageEnglish
Pages (from-to)10233-10237
Number of pages5
JournalTetrahedron
Volume60
Issue number45
DOIs
StatePublished - Nov 1 2004

Keywords

  • (Z)-β-Bromovinyl ketone
  • Baylis-Hillman adducts
  • Magnesium bromine
  • α,β-Acetylenic ketones

Fingerprint Dive into the research topics of 'Z/E stereoselective synthesis of β-bromo Baylis-Hillman ketones using MgBr <sub>2</sub> as promoter via a one-pot three-component reaction'. Together they form a unique fingerprint.

Cite this