The enantiomeric recognition of dihydropyrimidonic compounds by chiral selectors derived from 4- or 2-chloro-3,5-dinitrobenzoic acid

Gazić, Ivana; Kontrec, Darko; Lesac, Andreja; Vinković, Vladimir

doi:10.1016/j.tetasy.2005.01.042

Cited by 8 publications

(4 citation statements)

References 19 publications

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“…16 DHPMs are generally resolved poorer on polysaccharide-derived CSPs than on the brush-type CSPs reported here and earlier. 11 This refers to the coated as well as to immobilized polysaccharide-derived CSPs. 17 Here we should point out the example of very good resolution of compound DHPM 12, Monastrol, on CSPs 1-3.…”

Section: Resultsmentioning

confidence: 99%

Role of the weak interactions in enantiorecognition of racemic dihydropyrimidinones by novel brush‐type chiral stationary phases

2007

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The chiral discrimination ability of two recently prepared chiral stationary phases (CSP 1 and CSP 2), based on a leucine derived chiral selector, was tested for the enantiomers of dihydropyrimidone (DHPM) derivatives and compared with the commercially available Hyun-leucine CSP 3 and classical Pirkle-leucine CSP 4. By combining all of these CSPs, the enantiomers of all DHPM derivatives used in this study can be properly resolved. Particularly good enantioresolutions were achieved for thioureide derivatives, such as Monastrol. The results presented show that sulfur-aromatic interactions are meritorious for these very good separations.

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Section: Resultsmentioning

confidence: 99%

Role of the weak interactions in enantiorecognition of racemic dihydropyrimidinones by novel brush‐type chiral stationary phases

2007

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“…Synthetic pyrethroid insecticides were enantioresolved on a Sumichiral OA-2500-I CSP (213). Six new CSPs prepared from 4-or 2-chloro-3,5-dinitrobenzoic acid, L-alanine, and different π-donor aromatic units were used in the enantioseparation of 13 racemic dihydropyrimidonic analytes (214).…”

Section: High-performance Liquid Chromatographymentioning

confidence: 99%

Chiral Separations

Ward

2006

Anal. Chem.

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“…8 Prompted by the work of Malyshev and Vinogradov. 9 and Vinkovic and coworkers, 10 who used the 2-chloro-3,5-dinitrobenzoic acid unit for linking chiral selector and the support to prepare CSPs which possess excellent enantioselectivity for some racemic compounds, we decided to use the same unit for linking a chiral selector that contains two chiral centers to the supports for discovering even better CSP for the enantioselective and diastereoselective separation of pyrethroid insecticides by HPLC.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective and diastereoselective separation of synthetic pyrethroid insecticides on a novel chiral stationary phase by high‐performance liquid chromatography

Tan¹,

Hou²,

Wang³

2007

Chirality

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A novel chiral packing material for high-performance liquid chromatography (HPLC) was prepared by connecting (R)-1-phenyl-2-(4-methylphenyl) ethylamine (PTE) amide derivative of (S)-isoleucine to aminopropyl silica gel through 2-amino-3,5-dinitro-1-carboxamido-benzene unit. This chiral stationary phase was applied to the enantioselective and diastereoselective separation of five pyrethroid insecticides by HPLC under normal phase condition. To achieve satisfactory baseline separation an optimization of the variables of mobile phase composition was required. The two enantiomers of fenpropathrin and four stereoisomers of fenvalerate were baseline separated using hexane-1,2-dichloroethane-2-propanol as mobile phase. The results show that the enantioselectivity of CSP is better than Pirkle type 1-A column for these compounds. Only partial separations for the cypermethrin and cyfluthrin stereoisomers were observed. Seven peaks and eight peaks were observed for cypermethrin and cyfluthrin, respectively. The elution orders were assigned by using different stereoisomer-enriched products.

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The enantiomeric recognition of dihydropyrimidonic compounds by chiral selectors derived from 4- or 2-chloro-3,5-dinitrobenzoic acid

Cited by 8 publications

References 19 publications

Role of the weak interactions in enantiorecognition of racemic dihydropyrimidinones by novel brush‐type chiral stationary phases

Role of the weak interactions in enantiorecognition of racemic dihydropyrimidinones by novel brush‐type chiral stationary phases

Chiral Separations

Enantioselective and diastereoselective separation of synthetic pyrethroid insecticides on a novel chiral stationary phase by high‐performance liquid chromatography

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