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Chiral resolution information


Chiral resolution, or enantiomeric resolution,[1] is a process in stereochemistry for the separation of racemic mixture into their enantiomers.[2] It is an important tool in the production of optically active compounds, including drugs.[3] Another term with the same meaning is optical resolution.

The use of chiral resolution to obtain enantiomerically pure compounds has the disadvantage of necessarily discarding at least half of the starting racemic mixture. Asymmetric synthesis of one of the enantiomers is one means of avoiding this waste.

  1. ^ Kuhn, Reinhard.; Erni, Fritz.; Bereuter, Thomas.; Haeusler, Johannes. (1992-11-15). "Chiral recognition and enantiomeric resolution based on host-guest complexation with crown ethers in capillary zone electrophoresis". Analytical Chemistry. 64 (22): 2815–2820. doi:10.1021/ac00046a026.
  2. ^ Smith, Michael B.; March, Jerry (2007), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th ed.), New York: Wiley-Interscience, p. 173-179, ISBN 978-0-471-72091-1
  3. ^ William H. Porter (1991). "Resolution of chiral drugs" (PDF). Pure Appl. Chem. 63 (8): 1119–1122. doi:10.1351/pac199163081119. S2CID 35860450.

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Chiral resolution

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reaction with a chiral catalyst or reagent, resulting in an enantioenriched sample of the less reactive enantiomer. As opposed to chiral resolution, kinetic...

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reaction (or reaction sequence) in which one or more new elements of chirality are formed in a substrate molecule and which produces the stereoisomeric...

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Resolution

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reciprocal of the unit in the last place Resolution (beam engine), an early steam engine at Coalbrookdale Chiral resolution, a process in stereochemistry for...

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Racemic mixture

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racemate into its components, the individual enantiomers, is called a chiral resolution. Various methods exist for this separation, including crystallization...

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Amphetamine

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salt which is fractionally crystallized to yield dextroamphetamine. Chiral resolution remains the most economical method for obtaining optically pure amphetamine...

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Diastereomer

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knowledge is harnessed in chiral synthesis to separate a mixture of enantiomers. This is the principle behind chiral resolution. After preparing the diastereomers...

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Malic acid

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capacity was 5,000 tons per year. The enantiomers may be separated by chiral resolution of the racemic mixture. S-Malic acid is obtained by fermentation of...

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Planar chirality, also known as 2D chirality, is the special case of chirality for two dimensions. Most fundamentally, planar chirality is a mathematical...

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Stereochemistry

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Stereochemistry. Alkane stereochemistry Chiral resolution, which often involves crystallization Chirality (chemistry) (R/S, d/l) Chiral switch Skeletal formula#Stereochemistry...

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enantioselective analysis. Chiral analysis includes all analytical procedures focused on the characterization of the properties of chiral drugs. Chiral analysis is usually...

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absence of an effective enantiomeric environment (precursor, chiral catalyst, or kinetic resolution), separation of a racemic mixture into its enantiomeric...

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isolated by fractional distillation. The enantiomers are separated by chiral resolution in reaction with methyl benzoate, selective crystallisation followed...

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provided by Prelog a year earlier to quinotoxine (enantiopure after chiral resolution) that is described. Woodward and Doering argue that Rabe in 1918 already...

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Tremetone

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the final product was a racemate that would not suitably undergo chiral resolution. This prevented isolation of the natural levorotary enantiomer of...

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otherwise be chiral due to a nitrogen stereocenter, nitrogen inversion provides a low energy pathway for racemization, usually making chiral resolution impossible...

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Homochirality

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Homochirality is a uniformity of chirality, or handedness. Objects are chiral when they cannot be superposed on their mirror images. For example, the left...

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Crystallization

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amounts of energy to be supplied to the system. Abnormal grain growth Chiral resolution by crystallization Crystal habit Crystal structure Crystallite Fractional...

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the allyl alcohol 27. Chiral resolution of this racemic compound with digitonin produced chiral 28 and on Oppenauer oxidation chiral 29. Hydrogenation (Adams'...

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Galantamine total synthesis

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Chemical yield: 1.4%. In addition they isolated (−)-narwardine by chiral resolution from a mixture of racemic narwedine and 0.5 equivalents of (+)-galanthamine...

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technique to separate enantiomers of chiral molecules in the pharmaceutical and fine chemical industries (chiral resolution). The exact interplay of the mechanisms...

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cases are not chiral. Generally a chiral and/or bianisotropic electromagnetic response is a consequence of 3D geometrical chirality: 3D-chiral metamaterials...

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Remdesivir

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remdesivir. In the end, optically pure remdesivir can be obtained through chiral resolution methods.[citation needed] An in vitro study of remdesivir assessing...

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Brucine

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reactivity toward chromic acid. Since brucine is a large chiral molecule, it has been used in chiral resolution. Fisher first reported its use as a resolving agent...

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