An efficient synthesis of (R)- and (S)-2-(aminomethyl)piperidine dihydrochloride

Gildas Deniau, Thomas Moraux, David O'Hagan, Alexandra M. Z. Slawin

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

The synthesis of the dihydrochloride salts of (R)-1 and (S)-1 2-(aminomethyl)piperidine is reported starting from either (S) or (R) lysine, respectively. A key step in the synthetic protocol involves the in situ formation of aziridinium 8, which then undergoes an intramolecular ring opening with concomitant piperidinium ring formation, in a stereoselective manner. The route offers a practical synthesis of (R)-1 and (S)-1, and it should make them more accessible for exploration in asymmetric catalysis or as building blocks in pharmaceutical research. (C) 2008 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)2330-2333
Number of pages4
JournalTetrahedron: Asymmetry
Volume19
DOIs
Publication statusPublished - 6 Oct 2008

Keywords

  • BETA-AMINO ACIDS
  • AZIRIDINIUM IONS
  • ALCOHOLS
  • DERIVATIVES
  • PIPERIDINE
  • LIGAND

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