Preparation and application of a new doubly tethered chiral stationary phase containing N-CH3 amide linkage based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid |
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Authors: | Hyun Myung Ho Cho Yoon Jae Song Yanci Choi Hee Jung Kang Bu Sung |
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Affiliation: | Department of Chemistry, Chemistry Institute for Functional Materials, Pusan National University, Busan, Republic of Korea. mhhyun@pusan.ac.kr |
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Abstract: | A new doubly tethered chiral stationary phase (CSP 5) based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid was developed by attaching the second tethering group to silica gel through a carbon atom of the first tethering group of the corresponding singly tethered CSP (CSP 2) containing an N-CH3 tertiary amide linkage, which was previously developed in our laboratory, in order to enhance the CSP stability without the loss of chiral recognition efficiency. The new CSP was quite effective in the resolution of various racemic alpha-amino acids, amines, and amino alcohols, and the chiral recognition efficiency of the new CSP was even greater than that of the corresponding singly tethered CSP especially in terms of the resolution factors (RS). The stability of the new CSP was greater than that of the corresponding singly tethered CSP. The chromatographic resolution behaviors of the new CSP were generally consistent with those of the corresponding singly tethered CSP. |
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Keywords: | α‐amino acids chiral amines chiral amino alcohols chiral crown ether chiral resolution enantiomer separation liquid chromatography resolution of enantiomers |
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