Possibilities of Exploiting Kinetic Control in the Continuous Fractional Crystallization of Diastereomeric Mixtures

For rapid and kinetic control-influenced resolutions, it is advisable to choose a resolving agent with the highest possible eutectic composition (eeEuResAg). It may also be advantageous to add the crystalline resolving agent directly to the solution of the racemic compound. In addition, the use of a quasi-racemic resolving agent or amphoteric resolving agent can provide kinetic resolution. In some cases, the continuous fractional crystallization of diastereomeric salts requires the salt of the resolving agent (Ca2+, Na+, etc.) or other achiral additives (thiourea) that cause rapid crystallization and provide high diastereomeric purity. A further advantage may be the sequential use of the same resolving agent that is capable of forming crystalline diastereomers with both enantiomers when using kinetic control (tandem resolution).

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Prediction of the efficiency of diastereoisomer separation on the basis of the behaviour of enantiomeric mixtures

RSC Advances ◽

10.1039/c4ra00526k ◽

2014 ◽

Vol 4 (41) ◽

pp. 21254-21261 ◽

Cited By ~ 9

Author(s):

Emese Pálovics ◽

Zsolt Szeleczky ◽

Balázs Fődi ◽

Ferenc Faigl ◽

Elemér Fogassy

Keyword(s):

Eutectic Composition ◽

Racemic Compound ◽

Dominant Effect

The composition of a crystalline diastereoisomer (eeDIA) is determined either by the eutectic composition of the racemic compound (eeEuRac) or that of resolving agent (eeEuRes) and the higher ee value has the more dominant effect.

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A New Twist in Eutectic Composition: Deracemization of a Racemic Compound Amino Acid by Viedma Ripening and Temperature Fluctuation

Israel Journal of Chemistry ◽

10.1002/ijch.202100075 ◽

2021 ◽

Author(s):

Cristobal Viedma ◽

José Eugenio Ortiz

Keyword(s):

Amino Acid ◽

Temperature Fluctuation ◽

Eutectic Composition ◽

Racemic Compound

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Resolution by Formation and Fractional Crystallization of Diastereomeric Salts

CRC Handbook of Optical Resolutions via Diastereomeric Salt Formation ◽

10.1201/9781420042603-7 ◽

2001 ◽

pp. 23-64

Keyword(s):

Fractional Crystallization ◽

Diastereomeric Salts

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Esters of arylpropionic acids with 1,2:5,6-di-O-isopropylidene- and 1,2-O-isopropylidene-α-D-glucofuranose

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19870766 ◽

1987 ◽

Vol 52 (3) ◽

pp. 766-774 ◽

Cited By ~ 4

Author(s):

Jiří Svoboda ◽

Karel Čapek ◽

Jaroslav Paleček

Keyword(s):

Fractional Crystallization ◽

Kinetic Resolution ◽

Methyl Esters ◽

Optically Pure ◽

Derivatives Of

On fractional crystallization of 3-O-(2-(2-fluoro-4-biphenylyl)propionyl)-, 3-O-(2-(4-isobutylphenyl)propionyl)- and 3-O-(2-(6-methoxy-2-naphthyl)propionyl)-1,2 :5,6-di-O-isopropylidene-α-D-glucofuranoses V-VII optically pure R-diastereoisomers were isolated. The derivatives of 1,2-O-isopropylidene-α-D-glucofuranose obtained on partial deacetylation of esters V-VII were separated chromatographically to R and S-diastereoisomers. Their hydrolysis or transesterification afforded optically pure arylpropionic acids or their methyl esters, respectively. Kinetic resolution of the acids gives rise to esters V-VII enriched in R-diastereoisomer.

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Eutectic Composition of a Chiral Mixture Containing a Racemic Compound

Organic Process Research & Development ◽

10.1021/op700018h ◽

2007 ◽

Vol 11 (2) ◽

pp. 293-293

Author(s):

Yaling Wang ◽

Rosario LoBrutto ◽

Robert W. Wenslow ◽

Ivan Santos

Keyword(s):

Eutectic Composition ◽

Racemic Compound

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Effect of the Enantiomeric Ratio of Eutectics on the Results and Products of the Reactions Proceeding with the Participation of Enantiomers and Enantiomeric Mixtures

Chemistry ◽

10.3390/chemistry2030051 ◽

2020 ◽

Vol 2 (3) ◽

pp. 787-795

Author(s):

Emese Pálovics ◽

Dorottya Fruzsina Bánhegyi ◽

Elemér Fogassy

Keyword(s):

Charge Distribution ◽

Eutectic Composition ◽

The Self ◽

Combined Effect ◽

Chiral Molecule ◽

Racemic Compound ◽

Enantiomeric Ratio

This perspective is focused on the main parameters determining the results of crystallization of enantiomers or enantiomeric mixtures. It was shown that the ratio of supramolecular and helical associations depends on the eutectic composition of the corresponding enantiomeric mixture. The M and P ratios together with the self-disproportionation (SDE) of enantiomers define the reaction of the racemic compound with the resolving agent. Eventually, each chiral molecule reacts with at least two conformers with different degrees of M and P helicity. The combined effect of the configuration, charge distribution, constituent atoms, bonds, flexibility, and asymmetry of the molecules influencing their behavior was also summarized.

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