Regio- and Stereoselective Alkylation of Pyridine-N-oxides: Synthesis of Substituted Piperidines and Pyridines

Deepak Kumar Barange, Magnus T. Johnson, Andrew G. Cairns, Roger Olsson (Lead / Corresponding author), Fredrik Almqvist (Lead / Corresponding author)

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

Regio- and stereoselective addition of alkyl Grignard reagents to pyridine-N-oxides gave C2-alkylated N-hydroxy-1,2,5,6-tetrahydropyridines and trans-2,3-disubstituted N-hydroxy-1,2,5,6-tetrahydropyridines in good to excellent yields. These intermediates were aromatized or alternatively reduced in one-pot methodologies for efficient syntheses of alkylpyridines or piperidines, respectively. These reactions have a broad substrate scope and short reaction times.

Original languageEnglish
Pages (from-to)6228-6231
Number of pages4
JournalOrganic Letters
Volume18
Issue number24
Early online date28 Nov 2016
DOIs
Publication statusPublished - 16 Dec 2016

Keywords

  • Reagents
  • Stereoselectivity
  • Electrophiles
  • Alkyls
  • Piperidines

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