Enantioseparation of 3-hydroxycarboxylic acids via diastereomeric salt formation was demonstrated using 2-amino-1,2-diphenylethanol (ADPE) and cinchonidine as the resolving agents. Racemic 3-hydroxy-4-phenylbutanoic acid (-), 3-hydroxy-4-(4-chlorophenyl)butanoic acid (-), and 3-hydroxy-5-phenylpentanoic acid (-) were efficiently resolved using these resolving agents. Moreover, the successive crystallization of the less-soluble diastereomeric salt of and cinchonidine using EtOH yielded pure ()- · cinchonidine salt in a high yield. The crystal structures of less-soluble diastereomeric salts were elucidated and it was revealed that hydrogen bonding and CH/ interactions play an important role in reinforcing the structure of the less-soluble diastereomeric salts.
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| http://dx.doi.org/10.3390/molecules28010114 | DOI Listing |
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