Chiral differentiation of novel isoxazoline derivatives on “clicked” thioether and triazole bridged cyclodextrin chiral stationary phases

Abstract

This work first demonstrates the complete chiral resolution of novel isoxazoline derivatives on smartly designed triazole- and thioether-bridged native cyclodextrin (CD) chiral stationary phases (CSPs).

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

“…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.…”

Thioether bridged cationic cyclodextrin stationary phases: Effect of spacer length, selector concentration and rim functionalities on the enantioseparation

“…Mono-6 A -deoxy-(p-tolylsulfonyl)--cyclodextrin (TsO-CD) was synthesized according to the reported procedure [12]. All the isoxazoline racemic pairs used were synthesized according to our previously reported procedure [28]. All the other racemates were obtained from Energy-Chemical (Shanghai, China).…”

“…Encouraged by the effectiveness of thiol-ene reaction, our group reported a stable -CD-CSP by immobilizing 1-vinylimidazolium--CD tosylate to thiol silica via thiol-ene click reaction for efficient resolution of anti-charged analytes [27,28] and two novel multifunctional CD-CSPs with well-defined structures were further prepared via a similar approach for ultimate enantioseparation of a large group of enantiomer pairs [29].…”

Recent development of cationic cyclodextrins for chiral separation

“…The new CSP afforded enhanced chiral separation ability towards Dns-amino acids, carboxylic aryl compounds and flavonoids by HPLC compared with the CSP prepared through azide/alkynyl click reaction, due to strong electrostatic interactions. The chiral differentiation of 26 isoxazoline derivatives was also conducted on "clicked" thioether and triazole-bridged CD CSPs in HPLC [46]. Most of selected analytes could be well resolved (R s > 1.5) under reversed-phase mode for both CSPs.…”