Chromatographic Resolution of <i>α</i>‐Amino Acids by (<i>R</i>)‐(3,3'‐Halogen Substituted‐1,1'‐binaphthyl)‐20‐crown‐6 Stationary Phase in <scp>HPLC</scp>

Wu, Peng; Wu, Yuping; Zhang, Junhui; Lu, Zhenyu; Zhang, Mei; Chen, Xuexian

doi:10.1002/cjoc.201600664

Cited by 9 publications

(4 citation statements)

References 27 publications

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“…These compounds were used in combination with BH 3 ·THF to promote the asymmetric Diels–Alder reactions. ( R )- or ( S )- 133 were also used to prepare other BINOL-based compounds for various applications. − …”

Section: Ortho-lithiation At 3-positionmentioning

confidence: 99%

Regioselective Substitution of BINOL

2024

Chem. Rev.

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1,1′-Bi-2-naphthol (BINOL) has been extensively used as the chirality source in the fields of molecular recognition, asymmetric synthesis, and materials science. The direct electrophilic substitution at the aromatic rings of the optically active BINOL has been developed as one of the most convenient strategies to structurally modify BINOL for diverse applications. High regioselectivity has been achieved for the reaction of BINOL with electrophiles. Depending upon the reaction conditions and substitution patterns, various functional groups can be introduced to the specific positions, such as the 6-, 5-, 4-, and 3-positions, of BINOL. Ortho-lithiation at the 3-position directed by the functional groups at the 2-position of BINOL have been extensively used to prepare the 3- and 3,3′-substituted BINOLs. The use of transition metal-catalyzed C–H activation has also been explored to functionalize BINOL at the 3-, 4-, 5-, 6-, and 7-positions. These regioselective substitutions of BINOL have allowed the construction of tremendous amount of BINOL derivatives with fascinating structures and properties as reviewed in this article. Examples for the applications of the optically active BINOLs with varying substitutions in asymmetric catalysis, molecular recognition, chiral sensing and materials are also provided.

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Section: Ortho-lithiation At 3-positionmentioning

confidence: 99%

Regioselective Substitution of BINOL

2024

Chem. Rev.

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Section: Recent Applications Of Crown Ether-based Cspsmentioning

confidence: 99%

“…To improve the chiral recognition ability of the CROWNPAK CR(+) selector, three R-(3,3′-X-substituted-1,1′-binaphthyl)-20-crown-6 (X: Cl, Br or I) selectors (Figure 6) containing CSPs were synthesized and compared in the enantiomeric separation of α-amino acids [38]. For the investigated amino acids, Br-substituted CSP had the highest chiral recognition ability and it provided a better resolution than the commercially available CSP.…”

Section: Columnmentioning

confidence: 99%

Liquid Chromatographic Enantioseparations Utilizing Chiral Stationary Phases Based on Crown Ethers and Cyclofructans

et al. 2021

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Natural compounds can exist in different forms, where molecules possessing chirality play an essential role in living organisms. Currently, one of the most important tasks of modern analytical chemistry is the enantioseparation of chiral compounds, in particular, the enantiomers of compounds having biological and/or pharmaceutical activity. Whether the task is to analyze environmental or food samples or to develop an assay for drug control, well-reproducible, highly sensitive, stereoselective, and robust methods are required. High-performance liquid chromatography best meets these conditions. Nevertheless, in many cases, gas chromatography, supercritical fluid chromatography, or capillary electrophoresis can also offer a suitable solution. Amino acids, proteins, cyclodextrins, derivatized polysaccharides, macrocyclic glycopeptides, and ion exchangers can serve as efficient selectors in liquid chromatography, and they are quite frequently applied and reviewed. Crown ethers and cyclofructans possessing similar structural characteristics and selectivity in the enantiodiscrimination of different amine compounds are discussed less frequently. This review collects information on enantioseparations achieved recently with the use of chiral stationary phases based on crown ethers or cyclofructans, focusing on liquid chromatographic applications.

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“…Subsequently, our group synthesized different crown ethers using BINOL as a chiral source and systematically studied their utility for chiral separation. The chiral crown ethers HPLC stationary phases synthesized from BINOL exhibited excellent chiral separation capability, particularly of chiral resolution of amino acids [33].…”

Section: Introductionmentioning

confidence: 99%

Separation of enantiomers by open‐tubular capillary electrochromatography using (R)‐1,1′‐bi‐2‐naphthol derivatives as chiral stationary phases

Tang

Qin

et al. 2022

Separation Science Plus

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Bi-2-naphthol is a kind of commonly used chiral molecule that has been widely applied in the fields of molecular recognition, materials, and asymmetric synthesis. Since there are few examples of utilizing (R)-1,1′-bi-2-naphthol derivatives used as stationary phases to resolve chiral compounds by capillary electrochromatography, three The (R)-1,1′-bi-2-naphthol derivatives were synthesized and used as stationary phases to fabricate capillary columns for chiral separation. Some of the experimental parameters for enantiomer separations were optimized. the columns exhibited good enantioselectivity for chiral alcohols, amines, ketones, and so forth. The relative standard deviation of enantiomer retention time in run-to-run, day-to-day and column-to-column experiments were 1.02, 4.45 and 5.60% using the (R)-(3,3′-di-p-cyanophenyl)-2,2′-dimethoxyl-1,1′-binaphthalene coated column, and 2.38, 3.20 and 4.94% using the (R)-(3,3′-dip-acetylphenyl)-2,2′-dimethoxy-1,1′-binaphthalene coated column. The results indicated that the (R)-1,1′-bi-2-naphthol derivatives may have utility in capillary electrochromatography.

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Chromatographic Resolution of α‐Amino Acids by (R)‐(3,3'‐Halogen Substituted‐1,1'‐binaphthyl)‐20‐crown‐6 Stationary Phase in HPLC

Cited by 9 publications

References 27 publications

Regioselective Substitution of BINOL

Regioselective Substitution of BINOL

Liquid Chromatographic Enantioseparations Utilizing Chiral Stationary Phases Based on Crown Ethers and Cyclofructans

Separation of enantiomers by open‐tubular capillary electrochromatography using (R)‐1,1′‐bi‐2‐naphthol derivatives as chiral stationary phases

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