Chirality switching in the crystallization of 1-(4-chlorophenyl) ethylamine with binaphthoic acid by ketimine formation

Ying Ji Jin, Yunseo Choi, Qian Chen, Mukesh Eknath Shirbhate, Haofei Huang, Youngmee Kim, Sung Jin Kim, Moo Jin Jun, Eon Cheol Koo, Kwan Mook Kim

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Abstract

Axially chiral binaphthoic acid (BNA) was studied as a resolving agent for a stereoselective crystallization of 1-(4-chlorophenyl)ethylamine (CPEA). The diastereomeric pair of (R)-BNA/(S)-CPEA crystallizes in methylene chloride, on the other hand, the pair of (S)-BNA/(S)-CPEA crystallizes in acetone. The switch of the solubility of the diastereomeric pair is due to the imine formation with acetone. The very low solubility of the BNA/imine pair appears to be responsible for the fast and complete imine formation. The crystal structure of the BNA part in both crystals of the diastereomers maintains a same feature. Asymmetric chiral channels and pockets composed by intermolecular packing of BNA molecules appear in the crystal structures, and the robustness of them seem to contribute to the recognition of the chirality of CPEA with high selectivity.

Original languageEnglish
Pages (from-to)1690-1695
Number of pages6
JournalBulletin of the Korean Chemical Society
Volume37
Issue number10
DOIs
StatePublished - 1 Oct 2016

Keywords

  • Binaphthoic acid
  • Chirality switching
  • Ketimine
  • Stereoselective crystallization

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