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

Author(s): G. Deniau, T. Moraux, D. O'Hagan, A. M. Z. Slawin

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.

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ISBN: 0957-4166
Publication Year: 2008
Periodical: Tetrahedron-Asymmetry
Periodical Number: 19
Volume: 19
Pages: 2330-2333
Author Address: