Author(s)
G. Deniau, T. Moraux, D. O'Hagan, A. M. Z. Slawin
ISBN
0957-4166
Publication year
2008
Periodical
Tetrahedron-Asymmetry
Periodical Number
19
Volume
19
Pages
2330-2333
Author Address
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.