Preparation and enantioseparation of a mixed selector chiral stationary phase derived from benzoylated tartaric acid and 1,2-diphenylethylenediamine.
L-Dibenzoyl tartaric acid was mono-esterified with benzyl alcohol, and then chlorinated with SOCl(2) to give (2S,3S)-1-(benzyloxy)-4-chloro-1,4-dioxobutane-2,3-diyl dibenzoate (Selector 1). (1R,2R)-1,2-Diphenylethylenediamine was mono-functionalized with phenyl isocyanate and phenylene diisocyanate in sequence to give (1R,2R)-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.
Wei
Wen-Juan
WJ
Key Laboratory of Green Chemical Process of Ministry of Education, Hubei Key Laboratory of Novel Chemical Reactor and Green Chemical Technology, Wuhan Institute of Technology, Wuhan, China.
Deng
Hui-Wen
HW
Chen
Wei
W
Bai
Zheng-Wu
ZW
Li
Shi-Rong
SR
D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D005029:Ethylenediamines / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity; D013644:Tartrates / Q000737:chemistry*
D005029:Ethylenediamines; D013644:Tartrates; C007305:1,2-dianilinoethane; C029768:tartaric acid