Immobilization of (1S,2R)-(+)-2-amino-1,2-diphenylethanol derivates on aminated silica gel with different linkages as chiral stationary phases and their enantioseparation evaluation by HPLC.
A chiral selector was prepared through the reaction between (1S,2R)-(+)-2-amino-1,2-diphenylethanol and phenyl isocyanate. This selector was immobilized on aminated silica gel, respectively, with bifunctional group linkers of 1,4-phenylene diisocyanate, methylene-di-p-phenyl diisocyanate, and terephthaloyl chloride to produce corresponding three chiral stationary phases. The prepared compounds and chiral stationary phases were characterized by FT-IR, elemental analysis, (1)H NMR, and solid-state (1)H NMR. The enantioseparation ability of these chiral stationary phases was evaluated with structurally various chiral compounds. The chiral stationary phase prepared with 1,4-phenylene diisocyanate as linker showed excellent enantioseparation ability. The influence of different linkages on the enantioseparation was discussed.
Yin
Chuan-Qi
CQ
School of Chemical Engineering and Pharmacy, Wuhan Institute of Technology, Wuhan, China.
He
Bao-Jiang
BJ
Li
Shi-Rong
SR
Liu
Yong-Qiong
YQ
Bai
Zheng-Wu
ZW
D000577:Amides / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods; D002845:Chromatography / Q000379:methods; D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation; D004983:Ethanolamines / Q000737:chemistry*; D017953:Isocyanates / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D015394:Molecular Structure; D058428:Silica Gel; D012822:Silicon Dioxide / Q000737:chemistry; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism
C530675:2-amino-1,2-diphenylethanol; D000577:Amides; D004983:Ethanolamines; D017953:Isocyanates; C025319:phenyl isocyanate; D058428:Silica Gel; D012822:Silicon Dioxide