Role of Additives during Deracemization Using Temperature Cycling

Belletti, Giuseppe; Meekes, Hugo; Rutjes, Floris P. J. T.; Vlieg, E.

doi:10.1021/acs.cgd.8b00856

Cited by 24 publications

(33 citation statements)

References 24 publications

(34 reference statements)

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“…already showed that the presence of small, chiral impurities can steer the outcome of the deracemization and can speed up the process . As recently reported, a very small amount of chiral impurities can already be sufficient to halve the deracemization time …”

Section: Resultsmentioning

confidence: 82%

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Photoracemization‐Based Viedma Ripening of a BINOL Derivative

Belletti

Tortora

Mellema³

et al. 2019

Chemistry A European J

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Viedma ripening is ad eracemizationp rocess that has been used to deracemize ar ange of chiral molecules. The method hast wo major requirements:t he compound needs to crystallize as ac onglomerate and it needs to be racemizable under the crystallization conditions. Although conglomerate formation can be induced in different ways, the number of racemization methods is still ratherl imited. To extend the scope of Viedma ripening, in the present research we applied UV-light-induced racemization in a Viedmar ipening process, and report the successful deracemizationo faB INOL derivative crystallizing as ac onglomerate. Irradiation by UV light activatest he target compound in combination with an organic base, required to promote the excited-state proton transfer (ESPT), leadingt hereaftert o racemization. This offers an ew tool towards the development of Viedma ripening processes, by using ac heap and "green"c atalytic source like UV light to racemize suitable chiral compounds.

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Section: Resultsmentioning

confidence: 82%

“…[30] As recently reported, a very small amount of chiral impurities can already be sufficient to halve the deracemization time. [31]…”

Section: Deracemization Using Viedmar Ipeningmentioning

confidence: 99%

Photoracemization‐Based Viedma Ripening of a BINOL Derivative

Belletti

Tortora

Mellema³

et al. 2019

Chemistry A European J

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“…For example, temperature-cycle-induced deracemization (TCID) is a process that converts a racemic mixture of the substrate to a nearly pure enantiomer in the solid phase without any external chiral source through temperature cycling. 1,[6][7][8][9][10][11] Scheme 1. Schematic representations of PC, TCID, and SOAT process.…”

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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“…Although TCID features simple steps in its realization, the key elements of the controlling mechanism of this relatively recent deracemization technique have not been completely established yet. Operating parameters such as the impact of solid mass involved in the thermal cycles,– the amount of catalyst, the cooling rate, the suspension volume, the initial enantiomeric excess, the amplitude of the sweeps, the racemization rate, and the use of additives as growth inhibitors have been studied previously. Moreover, several computational studies have attributed the observed chiral enrichment to the crystallization step occurring during the cooling stage.…”

Section: Introductionmentioning

confidence: 99%

On the Effect of Secondary Nucleation on Deracemization through Temperature Cycles

Cameli

Horst

Steendam³

et al. 2020

Chemistry A European J

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Herein, the pivotal role of secondaryn ucleation in ac rystallization-enhanced deracemization process is reported. During this process, complete and rapid deracemization of chiral conglomerate crystalso fa ni soindolinone is attained through fast microwave-assistedt emperature cycling. Ap arametric study of the main factorst hat affect the occurrence of secondary nucleation in this process, namely agitation rate, suspension density,a nd solutes upersaturation, confirmst hat an enhanced stereoselective secondary nucleation rate maximizest he deracemizationr ate. Analysis of the systemd uring as ingle temperature cycle showed that, although stereoselective particlep roduction during the crystallization stage leadstoenantiomeric enrichment, undesired kinetic dissolution of smaller particleso ft he preferred enantiomero ccurs during the dissolution step. Therefore, secondary nucleationi sc rucial for the enhancemento fd eracemization through temperature cycles and as such should be considered in further design and optimization of this process, as well as in other temperature cyclingp rocesses commonly applied in particle engineering.

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Role of Additives during Deracemization Using Temperature Cycling

Cited by 24 publications

References 24 publications

Photoracemization‐Based Viedma Ripening of a BINOL Derivative

Photoracemization‐Based Viedma Ripening of a BINOL Derivative

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

On the Effect of Secondary Nucleation on Deracemization through Temperature Cycles

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