Preparation and Enantioseparation of a Mixed Selector Chiral Stationary Phase Derived from Benzoylated Tartaric Acid and 1,2-Diphenylethylenediamine
Preparation and Enantioseparation of a Mixed Selector Chiral Stationary Phase Derived from Benzoylated Tartaric Acid and 1,2-Diphenylethylenediamine
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苯甲酰化酒石酸和 1,2-二苯基乙二胺混合选择手性固定相的制备和对映体分离
DOI：
10.1002/chir.20799
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发表时间：
2010-06-01
期刊：
影响因子：
2
通讯作者：
Li, Shi-Rong
中科院分区：
文献类型：
--
作者：
Wei, Wen-Juan;Deng, Hui-Wen;Li, Shi-Rong
以L-二苯甲酰酒石酸为原料，与苯甲醇进行单酯化反应，再用氯化硫进行氯化反应，制得(2S，3S)-1-(benzyloxy)-4-chloro-1，4-dioxobutane-2，3-diyl二苯甲酸酯(选择剂1)。(1R，2R)-1，2-二苯基乙二胺与苯基异氰酸酯和苯二异氰酸酯依次单官能化得到(1R，2R)-1，2-二苯基-2-(3-苯基脲)乙基4-异氰基苯基脲(选择剂2)。将选择剂1和选择剂2分别固定在胺化硅胶上，制备了两种刷型单一选择剂手性固定相。将选择子1和选择子2同时固定在胺化硅胶上，得到混合选择剂CSP。研究了这些CSP对映体的拆分能力。选择剂1的CSP分离能力最强，而混合选择剂CSP的拆分能力相对较低。手性22：604-611,2010。(C)2009年Wiley-Liss，Inc.
L-Dibenzoyl tartaric acid was mono-esterified with benzyl alcohol, and then chlorinated with SOCl2 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. Chirality 22:604-611, 2010. (C) 2009 Wiley-Liss, Inc.