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.
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.
Hyun
Myung Ho
MH
Department of Chemistry, Chemistry Institute for Functional Materials, Pusan National University, Busan, Republic of Korea. mhhyun@pusan.ac.kr
Cho
Yoon Jae
YJ
Song
Yanci
Y
Choi
Hee Jung
HJ
Kang
Bu Sung
BS