The novel macrocyclic compounds as chiral solvating agents for determination of enantiomeric excess of carboxylic acids

Ma, Fengnian; Shen, Xiaochen; Ming, Xin; Wang, Junmei; Ouyang, Jun; Cong, Zixiang

doi:10.1016/j.tetasy.2008.06.012

Cited by 29 publications

(6 citation statements)

References 32 publications

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“…Commercially available chiral amines, such as phenethylamine and (pseudo)ephedrines, are generally not effective for acids due to the formation of ammonium carboxylate salts, which may not be soluble in the NMR solvent 17. Apart from macrocyclic receptors,18, 19 recent development of small‐molecule CSAs are dominated by diamine and/or amide derivatives 20–29…”

Section: Resultsmentioning

confidence: 99%

“…[17] Apart from macrocyclic receptors, [18,19] recent development of small-molecule CSAs are dominated by diamine and/or amide derivatives. For chiral HPLC and GC to be deployed for enantiomeric excess (ee, %) determination, the presence of a CO 2 H moiety in the analyte often requires derivatization into the ester or amide to alter its polarity and/or volatility for analysis.…”

Section: Synthesis Of Zphcsmentioning

confidence: 99%

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New Chiral Zwitterionic Phosphorus Heterocycles: Synthesis, Structure, Properties and Application as Chiral Solvating Agents

Sheshenev

Boltukhina

Grishina

et al. 2013

Chemistry A European J

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A family of new chiral zwitterionic phosphorus-containing heterocycles (zPHC) have been derived from methylene-bridged bis(imidazolines). These structures were unambiguously determined, including single-crystal XRD analysis for two compounds. The stability, acid/base and electronic properties of these dipolar phosphorus heterocycles were subsequently investigated. zPHCs can be successfully employed as a new class of chiral solvating agents for the enantiodifferentiation of chiral carboxylic and sulfonic acids by NMR spectroscopy. The stoichiometry and binding constants for the donor-acceptor complexes formed were established by NMR titration methods.

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Section: Resultsmentioning

confidence: 99%

Section: Synthesis Of Zphcsmentioning

confidence: 99%

New Chiral Zwitterionic Phosphorus Heterocycles: Synthesis, Structure, Properties and Application as Chiral Solvating Agents

Sheshenev

Boltukhina

Grishina

et al. 2013

Chemistry A European J

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“…General procedure for the synthesis of compounds 8-16. Compounds 8-16 were synthesized using a modified procedure originally reported by Zhang et al 22 To a suspension of appropriate aminonaphthol (1 mmol) and K 2 CO 3 1.38 g (10 mmol) in dry DMF (15 mL) was added a solution of p-t-butylcalix [4]arene dibromide derivatives (0.5 mmol) in dry DMF (15 mL) dropwise. The mixture was stirred at room temperature for 48 h. Then it was poured into 50 mL water and extracted with toluene (10 mL ¥ 3), washed with water (10 mL) and brine (10 mL).…”

Section: Synthesesmentioning

confidence: 99%

Synthesis of chiral calix[4]arenes bearing aminonaphthol moieties and their use in the enantiomeric recognition of carboxylic acids

2011

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Two armed chiral calix[4]arenes 8-16 functionalized at the lower rim with chiral aminonaphthol units have been prepared and the structures of these receptors characterized by FTIR, (1)H, and (13)C, DEPT and COSY NMR spectroscopy and elemental analysis. The enantioselective recognition of these receptors with various carboxylic acids has been studied by (1)H NMR and UV/Vis spectroscopy. The receptors exhibited different chiral recognition abilities towards the enantiomers of racemic materials and formed 2 : 1 or 1 : 1 complexes between host and guest. It was also demonstrated that chiral calix[4]arenes 9 and 16 could be used as chiral NMR solvating agents to determine the enantiomeric purity of mandelic acid.

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“…A correlation between the enantiodiscrimination (DDd) and the host/guest ratio was obtained considering the acidity of the carboxylic acid, as suggested by Zhang. 22 Upon increasing the strength of the acid, lower host : guest ratios were required to have the optimal separation of the two signals relative to the enantiomers of the acid. This could be explained by the fact that weaker acids (e.g.…”

Section: H Nmr Enantiodiscrimination Experimentsmentioning

confidence: 99%

C-hexaphenyl-substituted trianglamine as a chiral solvating agent for carboxylic acids

et al. 2011

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Chiral hexaazamacrocycles with a trianglamine structure and C(3)-symmetry, containing six ring substituents and twelve stereocenters have been tested as chiral solvating agents (CSAs) for α-substituted carboxylic acids. Excellent results have been obtained with a hexaphenyl-substituted macrocycle. The optimal ratio between the macrocycle and racemic acid, allowing for baseline separation of the enantiomers' signals in the (1)H NMR spectrum, was dependent on the type of acid, in particular on its degree of acidity. The analyte and the CSA could be separated and recovered by a simple acid-base extraction and reused without purification. The conformations of the free and protonated hexaamino macrocycles were inferred by CD spectroscopic studies and DFT calculations.

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The novel macrocyclic compounds as chiral solvating agents for determination of enantiomeric excess of carboxylic acids

Cited by 29 publications

References 32 publications

New Chiral Zwitterionic Phosphorus Heterocycles: Synthesis, Structure, Properties and Application as Chiral Solvating Agents

New Chiral Zwitterionic Phosphorus Heterocycles: Synthesis, Structure, Properties and Application as Chiral Solvating Agents

Synthesis of chiral calix[4]arenes bearing aminonaphthol moieties and their use in the enantiomeric recognition of carboxylic acids

C-hexaphenyl-substituted trianglamine as a chiral solvating agent for carboxylic acids

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