Enantiomeric enrichment of non-racemic mixtures of binaphthol with non-chiral packings

Nicoud, Roger‐Marc; Jaubert, Jean‐Noël; Rupprecht, Isabell; Kinkel, J.N.

doi:10.1002/(sici)1520-636x(1996)8:3<234::aid-chir2>3.0.co;2-h

Cited by 46 publications

(29 citation statements)

References 19 publications

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“…Nicoud et al . recorded 1 H‐NMR spectra of the pure enantiomer of 1,1′‐bi‐2‐naphthol ( S )‐ 11 or ( R )‐ 11 and of the racemic mixture ( RS )‐ 11 at different concentrations in deuteriochloroform.…”

Section: Support For the Concept Of Dimeric Enantiomeric Associatesmentioning

confidence: 99%

“…Nicoud et al ., based on their studies on enantioseparation of nonracemic mixture of ( S )‐(−)‐ 11 and ( R )‐(+)‐ 11 , proposed a theoretical model based on ee effects observed during HPLC experiments to predict the enantiomeric enrichment of a nonracemic mixture and to calculate precisely the retention time of each fraction. For this model, it was considered that enantiomeric enrichment of nonracemic mixtures was due to dimerization in the fluid phase and the dimers (i.e., the homo‐ and heteroenantiomeric associates) had different equilibrium constants and adsorptivity.…”

Section: Theoretical Models To Explain Enantioselective Effects In Amentioning

confidence: 99%

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Enantioseparations in Achiral Environments and Chromatographic Systems

Martens

Bhushan

2016

Israel Journal of Chemistry

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Since the very first resolution of racemic tartaric acid by Pasteur, the importance of resolution and methodology has been on a path of continuous understanding and expansion. The science and chemistry of achieving such targets has changed a lot. The advent of chromatography changed the direction by involving synthetic, semisynthetic, or naturally occurring chiral materials for a direct approach to resolution, where rapid and reversible association occurs to form diastereomers with different stabilities and partition coefficients responsible for overall enantioseparation. It has now reached a stage where the separation of excess enantiomers from nonracemic mixtures has been achieved in a totally achiral environment, which does not appear to be in line with the prevalent concepts of basic stereochemistry. Caution should be exercised when enantiomerically enriched mixtures – obtained by enantioselective synthesis – are chromatographed for purification in preparative organic synthesis.

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Section: Support For the Concept Of Dimeric Enantiomeric Associatesmentioning

confidence: 99%

Section: Theoretical Models To Explain Enantioselective Effects In Amentioning

confidence: 99%

Enantioseparations in Achiral Environments and Chromatographic Systems

Martens

Bhushan

2016

Israel Journal of Chemistry

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“…A fraction of pure enantiomer is always a mixture of the monomer and the corresponding homochiral dimer, but does not contain any heterochiral dimer. It was shown, that the separation of the excess enantiomer of a nonracemic feed mixture is the combination of two effects,20 the difference in reaction equilibrium constants of the homo‐ and heterochiral dimerization reaction, and the difference in the adsorptivity of the homo‐ and heterochiral dimers.…”

Section: Application To the Separation Of Binaphthol Enantiomersmentioning

confidence: 99%

Dynamics of reaction separation processes in the limit of chemical equilibrium

2005

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“…"separation of excess enantiomer", 6,8 "enantiomeric enrichment", [8][9][10][11][12][13][15][16] and "optical purification".…”

mentioning

confidence: 99%

“…It is worth mentioning that the results of experiments are supported by theoretical modelling of chromatographic behaviour of non-racemic compounds under various conditions of achiral chromatography. [43][44][45][46][47][48][49][50] The results of these experimental studies and theoretical calculations allow the formulation of the concept of the SDE-phoric groups as a structural element responsible for the occurrence of the SDE during achiral chromatography. [51][52][53][54][55][56][57][58][59][60][61] Considering the structure of the SDE-phoric moieties one can expect interesting properties for a chiral sulfinyl grouping or a chiral thioamide residue.…”

mentioning

confidence: 99%

Self-disproportionation of enantiomers (SDE) of chiral sulfur-containing compounds via achiral chromatography

Drabowicz¹,

Koprowski²,

Wzorek³

et al. 2017

Arkivoc

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This review presents a comprehensive, critical treatment of all the literature data related to the phenomenon of the SDE taking place during gravity-driven achiral chromatography of scalemic compounds bearing sulfoxide and thioamide functionalities. The discussion is focused on the SDE magnitude as a function of the structure iof the compound, composition of eluent and stationary phase, including some mechanistic details. An apparent possibility of application of the SDE phenomenon via achiral chromatography as a novel, emerging unconventional enantiomeric purification technique is also discussed.

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Enantiomeric enrichment of non-racemic mixtures of binaphthol with non-chiral packings

Cited by 46 publications

References 19 publications

Enantioseparations in Achiral Environments and Chromatographic Systems

Enantioseparations in Achiral Environments and Chromatographic Systems

Dynamics of reaction separation processes in the limit of chemical equilibrium

Self-disproportionation of enantiomers (SDE) of chiral sulfur-containing compounds via achiral chromatography

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