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Expeditious synthesis and chromatographic resolution of (+)‐ and (−)‐ trans ‐1‐benzylcyclohexan‐1,2‐diamine hydrochlorides
Author(s) -
Bisel Philippe,
Schlauch Michael,
Weckert Edgar,
Sin KweonSeok,
Frahm August Wilhelm
Publication year - 2001
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/1520-636x(2001)13:2<89::aid-chir1003>3.0.co;2-d
Subject(s) - chemistry , diamine , hydrogenolysis , enantiomer , imine , resolution (logic) , chromatography , enantiomeric excess , stereochemistry , medicinal chemistry , organic chemistry , enantioselective synthesis , catalysis , artificial intelligence , computer science
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. Chirality 13:89–93, 2001. © 2001 Wiley‐Liss, Inc.