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Preparation and enantioseparation of a mixed selector chiral stationary phase derived from benzoylated tartaric acid and 1,2‐diphenylethylenediamine
Author(s) -
Wei WenJuan,
Deng HuiWen,
Chen Wei,
Bai ZhengWu,
Li ShiRong
Publication year - 2010
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/chir.20799
Subject(s) - chemistry , tartaric acid , isocyanate , silica gel , chirality (physics) , chromatography , enantiomer , benzyl alcohol , organic chemistry , polymer chemistry , catalysis , polyurethane , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , citric acid , quark
L ‐Dibenzoyl tartaric acid was mono‐esterified with benzyl alcohol, and then chlorinated with SOCl 2 to give (2 S ,3 S )‐1‐(benzyloxy)‐4‐chloro‐1,4‐dioxobutane‐2,3‐diyl dibenzoate (Selector 1 ). (1 R ,2 R )‐1,2‐Diphenylethylenediamine was mono‐functionalized with phenyl isocyanate and phenylene diisocyanate in sequence to give (1 R ,2 R )‐1,2‐diphenyl‐2‐(3‐phenylureido)ethyl 4‐ isocyanatophenylurea (Selector 2 ). Two brush‐type chiral stationary phases (CSPs) of single selector were prepared by separately immobilizing selectors 1 and 2 on aminated silica gel. Selectors 1 and 2 were simultaneously immobilized on aminated silica gel to give a mixed selector CSP. The enantioseparation ability of these CSPs was studied. The CSP of selector 1 has strongest separation ability, while the enantioseparation ability of the mixed selector CSP is relatively lower. Chirality 2010. © 2009 Wiley‐Liss, Inc.