Gildas P Deniau, Thomas Moraux, D. O'Hagan
Oct 6, 2008
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Journal
Tetrahedron-asymmetry
Abstract
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.