Nitroaldol-reaction of aldehydes in the presence of non-activated Mg:Al 2:1 hydrotalcite; A possible new mechanism for the formation of 2-aryl-1,3-dinitropropanes

Agnieszka Cwik, Aliz Fuchs, Zoltán Hell, Jean Marc Clacens

Research output: Contribution to journalArticle

55 Citations (Scopus)

Abstract

Commercially available, non-activated 2:1 Mg:Al hydrotalcite catalyzes the nitroaldol reaction between a variety of aromatic and aliphatic aldehydes and simple nitroalkanes such as nitromethane and nitroethane. A new mechanism is proposed for the formation of the 1,3-dinitropropanes. The threo/erythro diastereoselectivity of the nitroethane-adducts was determined by 1H NMR spectroscopy and was found to range from 50:50 to 70:30. The substituents of the aromatic aldehydes influenced the isomer ratio.

Original languageEnglish
Pages (from-to)4015-4021
Number of pages7
JournalTetrahedron
Volume61
Issue number16
DOIs
Publication statusPublished - Apr 18 2005

Keywords

  • 1,3-Dinitropropanes
  • Diastereoselectivity
  • Henry reaction
  • Hydrotalcite
  • Mechanism

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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