Enantiomeric separations of α-aryl ketones with cyclofructan chiral stationary phases via high performance liquid chromatography and supercritical fluid chromatography

Breitbach, Anthony S.; Lim, Yeeun; Xu, Qing; Kürti, László; Armstrong, Daniel W.; Breitbach, Zachary S.

doi:10.1016/j.chroma.2015.11.069

Cited by 26 publications

(11 citation statements)

References 19 publications

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“…Figure 5 depicts the structures of CF6-P, CF6-RN and CF7-DMP. Afterwards, the same group also carried out numerous comparison studies on the chiral recognition ability of cyclofructan-based CSPs (IP-CF6, RN-CF6 and DMP-CF7, as well as cyclodextrin-based CSPs) for the separation of a wide range of racemic compounds, including some unique and novel compounds such as tetrahydrobenzimidazoles, biaryl atropisomers, ruthenium(II) polypyridyl complexes, 2-naphthol atropisomers, α-aryl ketones, and spirobrassinin [53,[58][59][60][61][62][63][64][65][66][67][68]. The research results showed that most of the chiral analytes studied were well separated on these F I G U R E 5 The structures of the cyclofructan-based CSPs used for IP-CF6, RN-CF6 and DMP-CF7 chiral selectors, which have good complementary enantioseparation for some analytes.…”

Section: Cyclofructans Derivatives As Chiral Stationary Phases For Hplcmentioning

confidence: 99%

Recent development trends for chiral stationary phases based on chitosan derivatives, cyclofructan derivatives and chiral porous materials in high performance liquid chromatography

Xie

Yuan

2018

J of Separation Science

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The separation of enantiomers by chromatographic methods, such as gas chromatography, high-performance liquid chromatography and capillary electrochromatography, has become an increasingly significant challenge over the past few decades due to the demand of pharmaceutical, agrochemical, and food analysis. Among these chromatographic resolution methods, high-performance liquid chromatography based on chiral stationary phases has become the most popular and effective method used for the analytical and preparative separation of optically active compounds. This review mainly focuses on the recent development trends for novel chiral stationary phases based on chitosan derivatives, cyclofructan derivatives, and chiral porous materials that include metal-organic frameworks and covalent organic frameworks in high-performance liquid chromatography. The enantioseparation performance and chiral recognition mechanisms of these newly developed chiral selectors toward enantiomers are discussed in detail.

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Section: Cyclofructans Derivatives As Chiral Stationary Phases For Hplcmentioning

confidence: 99%

Recent development trends for chiral stationary phases based on chitosan derivatives, cyclofructan derivatives and chiral porous materials in high performance liquid chromatography

Xie

Yuan

2018

J of Separation Science

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“…Cyclofructans belong to the macrocyclic oligosaccharides consisted of 6 or more β(2→1) linked d ‐fructofuranose units. Recently, derivatized cyclofructans, CF6 and CF7, with a high degree of selectivity toward a variety of chiral compounds have been used as chiral selectors in HPLC , CE , and SFC .…”

Section: Introductionmentioning

confidence: 99%

“…Cyclofructans belong to the macrocyclic oligosaccharides consisted of 6 or more ␤(2→1) linked Abbreviations: CF, cyclofructan; CSP, chiral stationary phase; DMP-CF7, dimethylphenyl carbamate cyclofructan 7; P-CF6, isopropyl carbamate cyclofructan 6; RN-CF6, R-naphthylethyl carbamate cyclofructan 6 D-fructofuranose units. Recently, derivatized cyclofructans, CF6 and CF7, with a high degree of selectivity toward a variety of chiral compounds have been used as chiral selectors in HPLC [8][9][10][11][12][13], CE [14,15], and SFC [16,17].…”

Section: Introductionmentioning

confidence: 99%

Enantiomeric separation of new phytoalexin analogs with cyclofructan chiral stationary phases in normal-phase mode

et al. 2016

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For the first time, three different derivatized cyclofructan chiral stationary phases were used for the direct high-performance liquid chromatographic enantiomeric separation of 11 new racemic analogs of a natural indole phytoalexin. This class of compounds is known to have significant antiproliferative activity and other potentially useful pharmacological properties. The effect of various experimental factors was investigated to optimize the separations in the normal-phase mode. It was found that the nature of polar modifier and additive in the mobile phase have significant impact on the enantioseparations. Better chiral recognition of analyzed compounds was achieved on (R)-naphthylethyl carbamate cyclofructan 6 than on isopropyl carbamate cyclofructan 6 and dimethylphenyl carbamate cyclofructan 7. The thermodynamic parameters showed that the chiral separation was enthalpy controlled in all cases.

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“…Chiral metal complexes, 16 crown ethers, 17 cyclodextrins, 18 cyclofructans, 19 antibiotics, 20 Pirkle-type receptors, 21 zwitterionic quinine-based selectors, 22 among others enter in this category. 23 (ii) Sorbents based on optically active polymers, which can be synthetic such as the molecularly imprinted polymers 24 or obtained from natural sources, e.g.…”

Section: Brief Overview Of Chiral Stationary Phasesmentioning

confidence: 99%

Determination of Enantioselectivities by Means of Chiral Stationary Phase HPLC in Order to Identify Effective Proline-Derived Organocatalysts

Vargas-Caporali¹,

Juaristi²

2017

J. Braz. Chem. Soc.

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The pyrrolidine fragment is a privileged scaffold within chiral ligands employed in coordination complexes exhibiting catalytic activity in asymmetric reactions and, more recently, as enantioselective organocatalysts per se. Likewise, the employment of (S)-proline as starting material constitutes the most direct form to synthesize those chiral derivatives. Afterwards, a preliminary evaluation of the catalytic performance of proline-derived compounds consists of screening many prochiral substrates in well standardized model reactions such as Michael additions and Mannich reactions, with the aim of identifying "broad spectrum" catalysts for more complex synthetic applications. Therefore, a central part of this process involves the fast and direct measurement of enantioselectivities of optically active adducts. The growing development of chiral stationary phases and thus, the wide commercial availability of chiral columns have consolidated high performance liquid chromatography (HPLC) as the preferred technique to identify the most effective catalysts.

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Enantiomeric separations of α-aryl ketones with cyclofructan chiral stationary phases via high performance liquid chromatography and supercritical fluid chromatography

Cited by 26 publications

References 19 publications

Recent development trends for chiral stationary phases based on chitosan derivatives, cyclofructan derivatives and chiral porous materials in high performance liquid chromatography

Recent development trends for chiral stationary phases based on chitosan derivatives, cyclofructan derivatives and chiral porous materials in high performance liquid chromatography

Enantiomeric separation of new phytoalexin analogs with cyclofructan chiral stationary phases in normal-phase mode

Determination of Enantioselectivities by Means of Chiral Stationary Phase HPLC in Order to Identify Effective Proline-Derived Organocatalysts

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