Deracemization of a Racemic Compound by Using Tailor‐Made Additives

Engwerda, Anthonius H. J.; Schayik, Pim van; Jagtenberg, Henjo; Meekes, Hugo; Rutjes, Floris P. J. T.; Vlieg, E.

doi:10.1002/chem.201706088

Cited by 14 publications

(8 citation statements)

References 32 publications

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“…The low productivity of TCID is obviously due to the associated long process times. Indeed, the usual minimum process duration for TCID is about 10 h. 7,8,16,17 In contrast, PC runs typically involve rapid cooling; thus, the process times are much shorter. It is therefore important to shorten process times to significantly improve the process productivities and achieve a process with high productivity.…”

Section: Introductionmentioning

confidence: 99%

Resolution of an Atropisomeric Naphthamide by Second-Order Asymmetric Transformation: A Highly Productive Technique

Oketani

Hoquante

Brandel

et al. 2019

Org. Process Res. Dev.

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Temperature-cycle-induced deracemization (TCID) has been widely studied in the field of chiral separation, ranging from fundamental research to applications. In this study, the secondorder asymmetric transformation (SOAT) of 2-methoxy-1-naphthamide in an azeotropic mixture of ethyl acetate and cyclohexane is compared with TCID, in terms of process productivity. The results indicate that the volumetric productivity using SOAT was over 100times higher than that using TCID, such that a scale-up by a factor of 10 was easily implemented.

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Section: Introductionmentioning

confidence: 99%

Resolution of an Atropisomeric Naphthamide by Second-Order Asymmetric Transformation: A Highly Productive Technique

Oketani

Hoquante

Brandel

et al. 2019

Org. Process Res. Dev.

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“…Any composition in undersaturated or saturated solutions will evolve towards the racemic composition because of racemization in the liquid phase. There have been many reports on the irreversible evolution to a single chirality in the solid state for racemizable conglomerate‐forming systems . As long as the system remains an undersaturated solution, the enantiomeric excess of the system remains zero.…”

Section: Resultsmentioning

confidence: 99%

Deracemization in a Complex Quaternary System with a Second‐Order Asymmetric Transformation by Using Phase Diagram Studies

Oketani

Marin

Tinnemans³

et al. 2019

Chemistry A European J

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A productive deracemization process based on a quaternary phase diagram study of a naphthamide derivative is reported. New racemic compounds of an atropisomeric naphthamide derivative have been discovered, and a quaternary phase diagram has been constructed that indicated that four solids are stable in a methanol/H2O solution. Based on the results of a heterogeneous equilibria study showing the stable domain of the conglomerate, a second‐order asymmetric transformation was achieved with up to 97 % ee. Furthermore, this methodology showcases the chiral separation of a stable racemic compound forming system and does not suffer from any of the typical limitations of deracemization, although application is still limited to conglomerate‐forming systems. We anticipate that this present study will serve as a fundamental model for the design of sophisticated chiral separation processes.

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“…Nevertheless, the prerequisite for a racemization step is a major limiting factor for applying Viedma ripening, and many attempts were made to overcome this bottleneck. Successful that resulted in complete deracemization were made through the combination of grinding with physical factors, such as temperature gradients [123], temperature cycling [124], chiral additives [125], UV-light [126], and continuous solvent exchange, with which the very important antimalaria drug Mefloquine was deracemized [127]. Moreover, Vlieg et al showed that Viedma ripening is also effective for obtaining a single enantiomer, not only for compounds with a single stereocenter, but also from a mixture of stereoisomers with two (or more) different stereocenters, in a process that should be preceded by epimerization of stereocenters, and crystallization of the most stable pair of enantiomers as a racemic conglomerate [128].…”

Section: Crystallization-assisted Chiral Resolution In Solid Phasementioning

confidence: 99%

Functional Chirality: From Small Molecules to Supramolecular Assemblies

Adawy

2022

Symmetry

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Many structures in nature look symmetric, but this is not completely accurate, because absolute symmetry is close to death. Chirality (handedness) is one form of living asymmetry. Chirality has been extensively investigated at different levels. Many rules were coined in attempts made for many decades to have control over the selection of handedness that seems to easily occur in nature. It is certain that if good control is realized on chirality, the roads will be ultimately open towards numerous developments in pharmaceutical, technological, and industrial applications. This tutorial review presents a report on chirality from single molecules to supramolecular assemblies. The realized functions are still in their infancy and have been scarcely converted into actual applications. This review provides an overview for starters in the chirality field of research on concepts, common methodologies, and outstanding accomplishments. It starts with an introductory section on the definitions and classifications of chirality at the different levels of molecular complexity, followed by highlighting the importance of chirality in biological systems and the different means of realizing chirality and its inversion in solid and solution-based systems at molecular and supramolecular levels. Chirality-relevant important findings and (bio-)technological applications are also reported accordingly.

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Deracemization of a Racemic Compound by Using Tailor‐Made Additives

Cited by 14 publications

References 32 publications

Resolution of an Atropisomeric Naphthamide by Second-Order Asymmetric Transformation: A Highly Productive Technique

Resolution of an Atropisomeric Naphthamide by Second-Order Asymmetric Transformation: A Highly Productive Technique

Deracemization in a Complex Quaternary System with a Second‐Order Asymmetric Transformation by Using Phase Diagram Studies

Functional Chirality: From Small Molecules to Supramolecular Assemblies

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