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Preparation and application of a new doubly tethered chiral stationary phase containing NCH 3 amide linkage based on (+)‐(18‐crown‐6)‐2,3,11,12‐tetracarboxylic acid
Author(s) -
Hyun Myung Ho,
Cho Yoon Jae,
Song Yanci,
Choi Hee Jung,
Kang Bu Sung
Publication year - 2006
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20346
Subject(s) - chemistry , amide , chiral stationary phase , resolution (logic) , kinetic resolution , amino acid , stereochemistry , phase (matter) , asymmetric carbon , carbon atom , linkage (software) , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis , optically active , ring (chemistry) , biochemistry , artificial intelligence , computer science , gene
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 NCH 3 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 α‐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 ( R S ). 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. Chirality, 2006. © 2006 Wiley‐Liss, Inc.