Tris[3-(tert-butylhydroxymethylene)-d-camphorato]europium(III). A reagent for determining enantiomeric purity

Whitesides, George M.; Lewis, Daniel W.

doi:10.1021/ja00726a049

Cited by 176 publications

(28 citation statements)

References 2 publications

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“…The most is that some of the involved experimental aspects may also be unknown a priori: for example, the composition of the most widely used CE chiral additives, i. e. the commercially available functionalized β-cyclodextrins, may considerably vary depending on the vendor and thus unforeseeably alter the results of the analyses. 52 Consequently, we turned our attention to 1 H-NMR spectroscopy methods based on diastereomeric complex formation between chiral amines and either chiral lanthanide shift reagents (CLSRs) 53 or chiral solvating agents (CSAs): 54 generally differences in the resonance signals from each enantiomer are observed and the relative area may be easily utilized to derive ee, provided that sufficient resolution of signals is obtained. However, only few examples of 1 H-NMR methods devoted to 1a ee determination are found in the literature, and the reported applications were tainted with some drawbacks.…”

Section: Constitute Amentioning

confidence: 99%

H-NMR determination of the enantiomeric excess of the antiarrhytmic drug Mexiletine by using mandelic acid analogues as chiral solvating agents

Carbonara¹,

Carocci²,

Fracchiolla³

et al. 2003

Arkivoc

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Several optically active mandelic acid analogues were shown to allow a direct 1 H-NMR determination of the enantiomeric composition of Mexiletine [1-(2,6-dimethylphenoxy)-2-propanamine], a chiral, orally effective antiarrhythmic agent, and some of its derivatives. Excellent results were obtained with few milligram samples, at room temperature in CDCl 3 , without the need of deconvolution software, and regardless of the instrument used (200 or 300 MHz).

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Section: Constitute Amentioning

confidence: 99%

H-NMR determination of the enantiomeric excess of the antiarrhytmic drug Mexiletine by using mandelic acid analogues as chiral solvating agents

Carbonara¹,

Carocci²,

Fracchiolla³

et al. 2003

Arkivoc

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“…Chiral LSR5, tris chelates of optically activefl_diketonate ligands with lanthanide ions, were introduced in 1970 [21] and since then have been extensively used to determine enantiomeric compositions.…”

Section: Lanthanide Shift Reagents (Lsrs)mentioning

confidence: 99%

Organic analytical reagents in nuclear magnetic resonance spectroscopy

Flockhart¹,

Burns²

1987

Pure and Applied Chemistry

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“…C 63,l H 7,06 N 8,7. (-)Sb: a = 5,8g(20mmol)(-)-angereichertes5b,b= 5,0g (14mmol) 2 H 7,18 N 8,7 Gef. C 63,3 H 7,12 N 8,8. 9 H 7,76 N 8,6 Gef.…”

Section: Racem 3-aminoethyl-3-cyclohexyl-1 -Methyl-pyrrolidin-25-dunclassified

Basisch substituierte Pyrrolidin‐2,5‐dione, 1. Mitt. Synthese racem. und optisch aktiver N‐Methylpyrrolidindione

Knabe

Konrad

1985

Archiv der Pharmazie

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Ausgehend von Phenyl-(1) und 2-Thienylbernsteinsaure (2) wurden iiber die 3-monosubstituierten Pyrrolidindione 3/4 die basisch substituierten Pyrrolidindione 9 6 synthetisiert. Durch katalytische Hydrierung der 3-Phenylverbindungen 5 wurden die 3-Cyclohexylpyrrolidindione 7 hergestellt . Die Enantiomere von 5a, 5b, 6a und 6b wurden durch Racematspaltung mit Binaphthylphosphorsaure, die von 5c und 5d durch Spaltung mit Camphersulfonsaure gewonnen. Die Enantiomere von 7a-7c lieferte die katalytische Hydrierung der Enantiomere von 5a-Sc. Pyrrolidine-2,s-diones with Basic Substituents, I: Syntheses of Racemic and Optically Active N- Meth ylpyrrolidinedionesStarting from phenyl-(1) or 2-thienylsuccinic acid (2) the pyrrolidinediones 516 with basic substituents are synthesized via the 3-monosubstituted pyrrolidinediones. By catalytic hydrogenation of the 3-phenyl compounds 5 the 3-cyclohexylpyrrolidinediones 7 are obtained. The enantiomers of Sa, Sb, 6a and 6b are obtained by resolution with binaphthylphosphoric acid, those of Sc and 5d with camphorsulfonic acid. The enantiomers of 7a-7c are obtained by catalytic hydrogenation of the enantiomers of 5a-5c. 0365-6233/85/1111-1015 S M.50/0 0 VCH Verlagsgerellschah rnbH, D-6940 Weinheirn, 1985

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Tris[3-(tert-butylhydroxymethylene)-d-camphorato]europium(III). A reagent for determining enantiomeric purity

Cited by 176 publications

References 2 publications

H-NMR determination of the enantiomeric excess of the antiarrhytmic drug Mexiletine by using mandelic acid analogues as chiral solvating agents

H-NMR determination of the enantiomeric excess of the antiarrhytmic drug Mexiletine by using mandelic acid analogues as chiral solvating agents

Organic analytical reagents in nuclear magnetic resonance spectroscopy

Basisch substituierte Pyrrolidin‐2,5‐dione, 1. Mitt. Synthese racem. und optisch aktiver N‐Methylpyrrolidindione

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