Facile and Highly Stereoselective One-Pot Synthesis of Either (E)- or (Z)-Nitro Alkenes

• Abstract
• Full Text HTML
• Hi-Res PDF[53 KB]
• PDF w/ Links[93 KB]

• Supporting Info
• Figures
• Citing Articles

Your current credentials do not allow retrieval of the full text.

Purchase the full-text

• PDF/HTML,
  figures/images,
  references and tables,
  (where available)

Abstract

Aliphatic aldehydes were reacted with nitro alkanes in the presence of catalytic amounts of piperidine over 4 Å molecular sieves. Simply by changing reaction conditions (solvent and temperature) it is possible to control the stereochemical outcome of the reactions, obtaining pure (E)- and (Z)-nitro alkenes in high to excellent yields. The role of molecular sieves on the stereochemical control seems crucial in addition to that of piperidine, especially for the synthesis of the Z isomer.

Citing Articles

View all 3 citing articles

Citation data is made available by participants in CrossRef's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search in SciFinder.

This article has been cited by 2 ACS Journal articles (2 most recent appear below).

• 

  Different Routes for Preparing Mesoporous Organosilicas Containing the Tröger’s Base and Their Textural and Catalytic Implications

  Evelyne Poli, Estíbaliz Merino, Urbano Díaz, Daniel Brunel, and Avelino Corma
  The Journal of Physical Chemistry C2011 115 (15), 7573-7585

  • Different Routes for Preparing Mesoporous Organosilicas Containing the Tröger’s Base and Their Textural and Catalytic Implications

    Evelyne Poli, Estíbaliz Merino, Urbano Díaz, Daniel Brunel, and Avelino Corma
    The Journal of Physical Chemistry C2011 115 (15), 7573-7585

    Organosilica materials with different contents of Tröger’s base (TB) as builder moieties have been synthesized from previously synthesized bis-trialkoxysilylated Tröger’s base. Three well-nanostructured hybrid mesoporous materials were prepared through ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Selective Nitroaldol Condensations over Heterogeneous Catalysts in the Presence of Supercritical Carbon Dioxide

  Roberto Ballini, Marco Noè, Alvise Perosa and Maurizio Selva
  The Journal of Organic Chemistry2008 73 (21), 8520-8528

  • Selective Nitroaldol Condensations over Heterogeneous Catalysts in the Presence of Supercritical Carbon Dioxide

    Roberto Ballini, Marco Noè, Alvise Perosa and Maurizio Selva
    The Journal of Organic Chemistry2008 73 (21), 8520-8528

    At 40−60 °C, in the presence of heterogeneous catalysts based on Al2O3, supercritical carbon dioxide not only acts as a good solvent for the reaction of aromatic and aliphatic aldehydes with 1-nitroalkanes but, most importantly, it also allows the ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

SciFinder Links

• Get Reference Detail
• Get Substances
• Get Reactions
• Get Cited
• Get Citing