Attrition-enhanced preferential crystallization combined with racemization leading to redissolution of the antipode nuclei

Levilain, Guillaume; Rougeot, Céline; Guillen, Frédéric; Plaquevent, Jean‐Christophe; Coquerel, Gérard

doi:10.1016/j.tetasy.2009.11.015

Cited by 37 publications

(34 citation statements)

References 8 publications

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“…[129] Further it could be shown, that implementation of grinding and in-situ racemization in preferential crystallization facilitates an improved process performance with respect to yield and productivity. [130] The more general exploitation of Viedma ripening as well as the extension of applicability of preferential crystallization to racemic compounds are expected to increase the attractiveness of both techniques for industrial scale enantiomer separation.…”

Section: Attrition-enhanced Deracemization (Viedma Ripening) Attritimentioning

confidence: 99%

Processes To Separate Enantiomers

2014

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The provision of pure enantiomers is of increasing importance not only for the pharmaceutical industry but also for agrochemistry and biotechnology. In general, there are two rival approaches to provide pure enantiomers. The "chiral" approach is based on developing an asymmetric synthesis of just one of the enantiomers, while the "racemic" approach is based on separating mixtures of the two enantiomers. In the last few years remarkable progress has been achieved in the latter area. This Review focuses in particular on enantioselective crystallization processes and preparative chromatography, including hybrid processes and the incorporation of racemization steps. Several examples from our research are used for illustration purposes.

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Section: Attrition-enhanced Deracemization (Viedma Ripening) Attritimentioning

confidence: 99%

Processes To Separate Enantiomers

2014

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“…It also provides a scenario for the evolution of single chirality as is found in nature. [12,[19][20][21][22][23] Furthermore, a wide variety of procedural approaches, including circularly polarized light, shifted crystal size distributions, and chiral additives have been shown to change at will a racemic mixture of conglomerate crystals to a predetermined handedness. [3,[23][24][25] Although the rate-determining parameters have been identified, pinning down the driving force for this asymmetric transformation has remained a challenge.…”

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confidence: 99%

The Driving Mechanism Behind Attrition‐Enhanced Deracemization

et al. 2010

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Change of heart: A solution‐phase enantiomeric excess that has the handedness of the minor population of the solid phase is observed during grinding of a slurry of racemic conglomerate crystals. This excess is the driving force for a net flux of molecules from crystals of the minor handedness to crystals of the major handedness, thus explaining the complete deracemization of the solid phase (see picture: blue: S form, red: R form).

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“…In attempt to explain NaClO 3 crystallization data, Kondepudi et al [66][67][68][69][70]73,74] and other researchers [75][76][77][78] attached importance to the experimental fact of stirring. To explain enantioselectivity of NaClO 3 land d-crystals stirring with and without glass beads (Figure 6a,c) many researchers [71,[79][80][81][82][83][84][85][86][87] argued that attrition/grinding was the key factor. Moreover, chiral enrichment vectors are the same in time but are manifested as stochastically (random) reactions, while enantioselectivity vectors are not the same for different enantiomers (Figure 8).…”

Section: Stirring (Helical Flux) Of the Reaction Mass As A Chirality mentioning

confidence: 99%

Сhiral and Racemic Fields Concept for Understanding of the Homochirality Origin, Asymmetric Catalysis, Chiral Superstructure Formation from Achiral Molecules, and B-Z DNA Conformational Transition

2019

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The four most important and well-studied phenomena of mirror symmetry breaking of molecules were analyzed for the first time in terms of available common features and regularities. Mirror symmetry breaking of the primary origin of biological homochirality requires the involvement of an external chiral inductor (environmental chirality). All reviewed mirror symmetry breaking phenomena were considered from that standpoint. A concept of chiral and racemic fields was highly helpful in this analysis. A chiral gravitational field in combination with a static magnetic field (Earth’s environmental conditions) may be regarded as a hypothetical long-term chiral inductor. Experimental evidences suggest a possible effect of the environmental chiral inductor as a chiral trigger on the mirror symmetry breaking effect. Also, this effect explains a conformational transition of the right-handed double DNA helix to the left-handed double DNA helix (B-Z DNA transition) as possible DNA damage.

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Attrition-enhanced preferential crystallization combined with racemization leading to redissolution of the antipode nuclei

Cited by 37 publications

References 8 publications

Processes To Separate Enantiomers

Processes To Separate Enantiomers

The Driving Mechanism Behind Attrition‐Enhanced Deracemization

Сhiral and Racemic Fields Concept for Understanding of the Homochirality Origin, Asymmetric Catalysis, Chiral Superstructure Formation from Achiral Molecules, and B-Z DNA Conformational Transition

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