Premium
Synthesis of regioselectively substituted cellulose derivatives and applications in chiral chromatography
Author(s) -
Acemoglu Murat,
Küsters Ernst,
Baumann Jürgen,
Hernandez Ivan,
Pong Mak Ching
Publication year - 1998
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/(sici)1520-636x(1998)10:4<294::aid-chir3>3.0.co;2-8
Subject(s) - cellulose , chemistry , regioselectivity , enantiomer , tris , organic chemistry , chirality (physics) , column chromatography , carbamate , catalysis , biochemistry , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
Various cellulose‐2,3‐bis‐arylcarbamate‐6‐O‐arylesters and cellulose‐2,3‐bis‐arylester‐6‐O‐arylcarbamates, designed to test the possible combined effects of the known tris‐arylcarbamate and tris‐arylester classes, were synthesized with high regioselectivity at O‐C(6), and their use as CSP s in liquid chromatography for enantiomeric separations was investigated. The separations obtained with the synthesized CSP s were compared to the separations achieved on a self‐packed reference column, consisting of cellulose‐tris‐(3,5‐dimethylphenyl‐carbamate) as CSP standard. Among the synthesized, regioselectively substituted cellulose derivatives, 2,3‐bis‐O‐(3,5‐dimethylphenylcarbamate)‐6‐O‐benzoate‐cellulose and 2,3‐bis‐O‐(benzoate)‐6‐O‐(3,5‐dichlorophenylcarbamate)‐cellulose gave the best CSP s for the separation of the test racemates. CSP s from regioselectively substituted cellulose derivatives seem to exhibit higher selectivities than cellulose‐tris‐(3,5‐dimethylphenylcarbamate) for certain classes of racemic compounds. Chirality 10:294–306, 1998. © 1998 Wiley‐Liss, Inc.