Measurement and modeling of the equilibrium behavior of the Tröger’s base enantiomers on an amylose-based chiral stationary phase

Mihlbachler, Kathleen; Kaczmarski, Krzysztof; Seidel‐Morgenstern, A.; Guiochon, Georges

doi:10.1016/s0021-9673(02)00228-5

Cited by 92 publications

(53 citation statements)

References 20 publications

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“…The thermodynamics and kinetics of the adsorption and mass transfer of the Tröger base were studied in great detail. 20,21 However, to our surprise, studies on the chiral chromatography of functionalized derivatives of the Tröger base are limited to a single example. 22 Recently, we have separated enantiomers of bismalonate derivatives of the Tröger base and applied them to the regio-and stereoselective tether-directed remote functionalization of fullerenes.…”

Section: Introductionmentioning

confidence: 99%

Semipreparative enantioseparation of Tröger base derivatives by HPLC

Sergeyev

Diederich

2006

Chirality

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We describe the enantioseparation of functionalized derivatives of the Tröger base by HPLC on commercially available chiral stationary phases. Cellulose-derived Chiralcel OJ and brush-type Whelk O1 are demonstrated to be complementary to each other in their scope. On the basis of the results obtained, the separation of selected compounds was successfully transferred onto semipreparative columns. We believe that the availability of enantiopure functionalized derivatives of the Tröger base will stimulate the further use of this interesting molecular scaffold in molecular recognition, asymmetric catalysis, and related areas of research and technology.

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Section: Introductionmentioning

confidence: 99%

Semipreparative enantioseparation of Tröger base derivatives by HPLC

Sergeyev

Diederich

2006

Chirality

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“…In the binary chromatogram, the two components overlap much more than in the first example, but less than one could imagine in the case of species sharing the same value of the Henry's constant (under analytical, infinite dilution conditions, the two species would elute together and would be indistinguishable). This is a quite remarkable behavior, a practical example of which has been investigated and reported earlier [12].…”

Section: Resultsmentioning

confidence: 63%

A Method for Deriving Explicit Binary Isotherms Obeying the Ideal Adsorbed Solution Theory

Tarafder¹,

Mazzotti²

2011

Chem Eng & Technol

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A method to derive explicit binary isotherms following the ideal adsorbed solution (IAS) theory is proposed. The method is applicable to any pair of singlecomponent isotherms, as long as they fulfill a set of conditions, as described in this report. Examples of some isotherms fulfilling such conditions are: Langmuir, anti-Langmuir, Brunauer-Emmett-Teller (BET), and quadratic. Following the method proposed in this report, three previously unreported explicit binary isotherms, quadratic-BET, quadratic-Langmuir, and quadratic-anti-Langmuir, while following the IAS framework, could be derived. This work presents the method and the binary isotherms derived through this method.

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“…[293] Weitere Arbeiten hinsichtlich der thermodynamischen Charakterisierung dieses anspruchsvollen Chromatographiesystems und erste Versuche, das Verhalten basierend auf molekularen Simulationen zu erklären, sind in Lit. [294,295] zu finden.…”

Section: Beispiele Präparativer Chromatographischer Enantiomerentrennunclassified

Verfahren zur Enantiomerentrennung

Lorenz

Seidel‐Morgenstern

2014

Angewandte Chemie

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Die Verfügbarkeit reiner Enantiomere ist von steigender Bedeutung für die pharmazeutische Industrie sowie auch für die Agrochemie und Biotechnologie. Generell gibt es zwei konkurrierende Ansätze zur Gewinnung von reinen Enantiomeren. Der “chirale” Ansatz basiert auf der Entwicklung einer asymmetrischen Synthese, die selektiv eines der Enantiomere liefert. Der “racemische” Ansatz basiert auf der Trennung eines Gemischs der beiden Enantiomere, wobei hier in den letzten Jahren bemerkenswerte Fortschritte erzielt werden konnten. Dieser Aufsatz fokussiert insbesondere auf enantioselektive Kristallisationsprozesse und präparative Chromatographie, einschließlich hybrider Trennprozesse und der zusätzlichen Integration von Racemisierungsschritten. Zur Illustration dienen mehrere in unserem Arbeitskreis untersuchte Trennungen.

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Measurement and modeling of the equilibrium behavior of the Tröger’s base enantiomers on an amylose-based chiral stationary phase

Cited by 92 publications

References 20 publications

Semipreparative enantioseparation of Tröger base derivatives by HPLC

Semipreparative enantioseparation of Tröger base derivatives by HPLC

A Method for Deriving Explicit Binary Isotherms Obeying the Ideal Adsorbed Solution Theory

Verfahren zur Enantiomerentrennung

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