Reactions between Grignard reagents and heterocyclic N-oxides: Stereoselective synthesis of substituted pyridines, piperidines, and piperazines

Research output: Contribution to journalReview article


In this perspective we discuss the recent developments of stereoselective synthesis of substituted pyridines, piperidines, and piperazines from cheap and commercially readily available starting materials. Pyridine N-oxides and pyrazine N-oxides are reacted with alkyl, aryl, alkynyl and vinyl Grignard reagents to give a diverse set of heterocycles in high yields. Optically active substituted piperazines are obtained by an asymmetric reaction from pyrazine N-oxides using sparteine as chiral ligand. In addition, a stereoselective synthesis of dienal-oximes from the reaction between pyridine N-oxides and Grignard reagents is presented, which results in a useful intermediate for the synthesis of a diverse set of compounds.


External organisations
  • Umeå University
  • ACADIA Pharmaceuticals AB
  • University of Gothenburg
Research areas and keywords

Subject classification (UKÄ) – MANDATORY

  • Organic Chemistry
  • Medicinal Chemistry
Original languageEnglish
Pages (from-to)337-346
Number of pages10
JournalOrganic and Biomolecular Chemistry
Issue number2
Publication statusPublished - 2011 Jan 21
Publication categoryResearch
Externally publishedYes