Chiral Resolution via Cocrystallization with Inorganic Salts

The coordination mode to lithium, magnesium, calcium and zinc cations of racemic vs. enantiopure amino acids and racetam APIs is analysed and its effect on chiral selection critically reviewed. It is shown that chiral resolution in the solid state can be obtained via cocrystallization of racemic com...

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Bibliographic Details
Published inIsrael journal of chemistry Vol. 61; no. 9-10; pp. 563 - 572
Main Authors Shemchuk, Oleksii, Grepioni, Fabrizia, Leyssens, Tom, Braga, Dario
Format Journal Article
LanguageEnglish
Published Haifa Wiley Subscription Services, Inc 01.10.2021
Subjects
Alkaline earth metals
Amino acids
Calcium ions
Cations
Chiral resolution
Cocrystallization
Coordination
Crystals
Inorganic salts
Lithium
Magnesium
racetams
Solid state
zinc
Zinc chloride
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Summary:The coordination mode to lithium, magnesium, calcium and zinc cations of racemic vs. enantiopure amino acids and racetam APIs is analysed and its effect on chiral selection critically reviewed. It is shown that chiral resolution in the solid state can be obtained via cocrystallization of racemic compounds with an achiral inorganic salt coformer, such as LiX (X=Cl, Br, I) or ZnCl2, which favour tetrahedral coordination in the solid state. The chiral selection may take the form of conglomerate crystal formation or of selective homochiral aggregation in racemic crystals. When cocrystallization involves alkaline earth metal cations, such as Ca2+ and Mg2+, which favour octahedral coordination, heterochiral complexation is observed in most cases, with formation of racemic crystals.
ISSN:0021-2148
1869-5868
DOI:10.1002/ijch.202100049