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1 2015

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Rozdzielenie mieszanin racemicznych za pomocą krystalizacji. Część 2, Rozdzielenie racematów z utworzeniem diastereoizomerycznych soli

Kołodziejska R., Studzińska R., Kopkowska E., Karczmarska-Wódzka A., Augustyńska B.

Wiadomości Chemiczne

2015

[Z] 69, 1-2

89--110

The enantioseparation of a racemate through diastereomeric salt formation with a resolving agent is one of the most attractive methods for obtaining an enantiopure compound, with advantages such as its simplicity in operation, recyclability of the chiral source, and applicability on an industrial scale. In this method the enantiomers are converted into a diastereomeric salt pair by reaction with a single enantiomer of resolving agent. The diastereomers are then separated by crystallization taking advantage of the different solubility of the two compounds [1–3]. The formation of diastereomers, to be separated afterward, usually consists of salt formation with a resolving agent of opposite acide-base character (Scheme 1, 9). In this process, the molecules of opposite character (amine and acid) recognize each other by various interactions on the basis of their molecular structures and functional groups [3]. Using this method can be obtained a series of enantiomerically pure amines (Scheme 2–8) [4–26] and acids (Scheme 10–17) [27–41] which may be valuable substrates for asymmetric synthesis. The conditions for enantioseparation play an important role. On the efficiency of the enantioseparation has an effect the resolving agent, nature of the solvent or just its dielectric constant and the character and amount of some supplementary additives.