Enantioseparation of isoxazolines with functionalized perphenylcarbamate cyclodextrin clicked chiral stationary phases in HPLC

Yang, Bo; Zhou, Jie; Wang, Yong; Tang, Jian; Tang, Weihua

doi:10.1002/elps.201600491

Cited by 7 publications

(2 citation statements)

References 33 publications

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“…Recently, the thiol‐ene reaction has attracted growing attention as it avoids the use of metal catalysts in Cu(I) catalytic 1,3‐dipolar cycloaddition, and it is used extensively for the development of chiral separation materials . Based on this art, our group developed a series cationic CD‐CSP by thiol‐ene click chemistry and confirmed its improved separation performance in LC . The CSP shows high enantioseparation ability to carboxylic aryl compounds, dansyl amino acids, isoxazolines, flavonoids, and so on in chiral HPLC.…”

Section: Introductionmentioning

confidence: 92%

Thiol‐ene click derived structurally well‐defined per(3,5‐dimethyl)phenylcarbamoylated cationic cyclodextrin separation material for achiral and chiral chromatography

Tang

Sun

et al. 2018

J of Separation Science

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In this work, a novel single sulfoether-bridged cationic per(3,5-dimethyl)phenylcarbamoylated-β-cyclodextrin separation material was prepared by thiol-ene click chemistry and characterized by using FTIR spectroscopy, solid-state C NMR spectroscopy and elemental analysis, which confirmed the correct structure. The separation material exhibited a good achiral separation performance for benzene homologues and phenylamine analogs, especially o-xylene and m-xylene, and m-phenylenediamine and o-phenylenediamine can be discriminated by the (3,5-dimethyl)phenylcarbamoyl cyclodextrins. The chiral resolving ability of the separation material was evaluated by discriminating various isoxazolines, flavonoids, and β-blockers in reversed-phase high-performance liquid chromatography. For isoxazolines, the material showed the best chiral discrimination toward 3-aryl-5-(2-oxopyrrolidin-1-yl)-isoxazolines, where the resolution for 3ClPh-OPr reached 6.03. For flavonoids, it exhibited more efficient separation to the ones with more hydrophobic substituents, with a resolution of 5.93 for 6-hydroxyflavanone. β-Blockers were also enantioseparated satisfactorily on the material. The as-prepared separation material is a good member of the thiol-ene click derived cyclodextrin stationary phase family.

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Section: Introductionmentioning

confidence: 92%

Thiol‐ene click derived structurally well‐defined per(3,5‐dimethyl)phenylcarbamoylated cationic cyclodextrin separation material for achiral and chiral chromatography

Tang

Sun

et al. 2018

J of Separation Science

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“…Moreover, the hydroxyl residues in the partially‐substituted β‐CD also enabled BACD‐HPS and MP‐CD‐HPS to be used under both normal and reversed‐phase conditions. Recently, it was reported that the enantioselectivity of the phenylcarbamate‐β‐CD‐based CSPs could be easily and flexibly adjusted when using chlorine and methyl functional groups to modify the phenylcarbamate moieties in the CSPs . Therefore, it is our interest to prepare a new type of partially‐substituted chlorine and methyl containing phenylcarbamate‐β‐CD‐bonded phase and to investigate its chromatographic performance in HPLC.…”

Section: Introductionmentioning

confidence: 99%

Preparation and evaluation of partially‐substituted 3‐chloro‐4‐methylphenylcarbamate‐β‐cyclodextrin bonded silica particles as chiral stationary phase for multi‐mode HPLC

Meng

et al. 2019

Separation Science Plus

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3‐Chloro‐4‐methylphenylcarbamate‐(3‐(2‐O‐β‐cyclodextrin)‐2‐hydroxypropoxy)‐propylsilyl‐appended silica particles (CMP‐CD‐HPS), a new type of partially‐substituted cyclodextrin‐bonded phase, have been successfully synthesized and applied as a chiral stationary phase in high‐performance liquid chromatography under multi‐mode conditions including normal phase, reversed phase, and polar organic mobile phase conditions. Chemical characterization for the CMP‐CD‐HPS was carried out by elemental analysis. The chromatographic performance of CMP‐CD‐HPS‐packed column was evaluated by separating the positional isomers of nitrophenol and nitraniline and the enantiomers of some chiral drug compounds. The separation results show that CMP‐CD‐HPS exhibited excellent selectivity for separating the positional isomers of disubstituted benzenes and the enantiomers of the chiral drugs. The hydroxyl residues of partially‐substituted β‐cyclodextrin and the stable spacer linking to secondary hydroxyl site of the β‐cyclodextrin in the new CMP‐CD‐HPS phase play important roles in the chromatographic separations.

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Preparation and Application of Partially Substituted Phenylcarbamate-(3-(2-O-β-cyclodextrin)-2-hydroxypropoxy)-propylsilyl-Appended Silica Particles as Chiral Stationary Phase for Multi-mode HPLC

Wang

et al. 2020

Chromatographia

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Enantioseparation of isoxazolines with functionalized perphenylcarbamate cyclodextrin clicked chiral stationary phases in HPLC

Cited by 7 publications

References 33 publications

Thiol‐ene click derived structurally well‐defined per(3,5‐dimethyl)phenylcarbamoylated cationic cyclodextrin separation material for achiral and chiral chromatography

Thiol‐ene click derived structurally well‐defined per(3,5‐dimethyl)phenylcarbamoylated cationic cyclodextrin separation material for achiral and chiral chromatography

Preparation and evaluation of partially‐substituted 3‐chloro‐4‐methylphenylcarbamate‐β‐cyclodextrin bonded silica particles as chiral stationary phase for multi‐mode HPLC

Preparation and Application of Partially Substituted Phenylcarbamate-(3-(2-O-β-cyclodextrin)-2-hydroxypropoxy)-propylsilyl-Appended Silica Particles as Chiral Stationary Phase for Multi-mode HPLC

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