Expeditious synthesis and chromatographic resolution of (+)- and (-)-trans-1-benzylcyclohexan-1,2-diamine hydrochlorides

Authors
Bisel, P Schlauch, M Weckert, E Sin, KS Frahm, AW
Citation
P. Bisel et al., Expeditious synthesis and chromatographic resolution of (+)- and (-)-trans-1-benzylcyclohexan-1,2-diamine hydrochlorides, CHIRALITY, 13(2), 2000, pp. 89-93
Citations number
19
Categorie Soggetti
Chemistry & Analysis
Journal title
CHIRALITY
ISSN journal
08990042 → ACNP
Volume
13
Issue
2
Year of publication
2000
Pages
89 - 93
Database
ISI
SICI code
0899-0042(2000)13:2<89:ESACRO>2.0.ZU;2-7
Abstract
The hitherto unknown (-)- and (+)-1-benzylcyclohexan-1,2-diamine hydrochlor ides 4a . HCl and 4b . HCl were synthesized by means of diastereoselective alpha -iminoamine rearrangement with subsequent imine reduction and hydroge nolysis. The relative trans-configuration as well as the absolute (1S,2R) a nd (1R,2S) configurations of 4a and 4b, respectively, were elucidated on th e basis of an X-ray analysis of 3b . HCl. The enantiomeric excess (ee) valu es of the title compounds (>99% )were determined by chiral HPLC on a Chirex (D) Penicillamine column. Chirality 13:89-93, 2001. (C) 2001 Wiley-Liss. I nc.