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

Bisel, Philippe; Schlauch, Michael; Weckert, Edgar F.; Sin, Kweon Seok; Frahm, August Wilhelm

doi:10.1002/1520-636X(2001)13:2<89::AID-CHIR1003>3.0.CO;2-D

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

Bisel, Philippe;
Schlauch, Michael;
Weckert, Edgar F.;
Sin, Kweon Seok;
Frahm, August Wilhelm

Citations

SCOPUS

4

초록

The hitherto unknown (-)- and (+)-1-benzylcyclohexan-1,2-diamine hydrochlorides 4a · HCl and 4b · HCl were synthesized by means of diastereoselective α-iminoamine rearrangement with subsequent imine reduction and hydrogenolysis. The relative trans-configuration as well as the absolute (1S,2R) and (1R,2S) configurations of 4a and 4b, respectively, were elucidated on the basis of an X-ray analysis of 3b · HCl. The enantiomeric excess (ee) values of the title compounds (>99%) were determined by chiral HPLC on a Chirex (D) Penicillamine column. © 2001 Wiley-Liss, Inc.

키워드

Chiral HPLC; Enantiomer resolution; Enantiopure compounds; Iminoamine rearrangement; Vicinal diamines; X-ray crystallography

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

저자: Bisel, Philippe; Schlauch, Michael; Weckert, Edgar F.; Sin, Kweon Seok; Frahm, August Wilhelm

DOI: 10.1002/1520-636X(2001)13:2<89::AID-CHIR1003>3.0.CO;2-D

발행일: 2001

유형: Article

저널명: Chirality

권: 13

호: 2

페이지: 89 ~ 93