Anti-selective and regioselective aldol addition of ketones with aldehydes using MgI 2 as promoter

Han Xun Wei, Richard L. Jasoni, Huawu Shao, Jiali Hu, Paul W. Paré

Research output: Contribution to journalArticlepeer-review

29 Scopus citations

Abstract

The first example of a direct aldehyde-ketone coupling using the secondary amine piperidine as base in the presence of MgI 2 to generate high selectivity of anti-aldol products from unmodified ethyl ketones in high yield is reported. The coupling reactions were carried out in a one-pot reaction by mixing four reaction components at room temperature. In the case of unsymmetrical ketones, addition was made to the less hindered α-side. Graphical Abstract

Original languageEnglish
Pages (from-to)11829-11835
Number of pages7
JournalTetrahedron
Volume60
Issue number51
DOIs
StatePublished - Dec 13 2004

Keywords

  • Anti-aldol reaction
  • Ethyl ketone
  • Magnesium iodide
  • Piperidine

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