标题：Chirality Switching in the Crystallization of 1-(4-Chlorophenyl)ethylamine with Binaphthoic Acid by Ketimine Formation
作者：Jin, Ying-Ji; Choi, Yunseo; Chen, Qian; Shirbhate, Mukesh Eknath; Huang, Haofei; Kim, Youngmee; Kim, Sung-Jin; Jun, Moo-Jin; Koo, Eon 更多 作者机构：[Jin, Ying-Ji; Choi, Yunseo; Chen, Qian; Shirbhate, Mukesh Eknath; Kim, Youngmee; Kim, Sung-Jin; Kim, Kwan Mook] Ewha Womans Univ, Dept Chem, Seoul 12 更多 通讯作者地址：[Kim, KM]Ewha Womans Univ, Dept Chem, Seoul 120750, South Korea;[Kim, KM]Ewha Womans Univ, Div Nano Sci, Seoul 120750, South Korea;[Huang, HF]Shandong 更多
来源：BULLETIN OF THE KOREAN CHEMICAL SOCIETY
关键词：Chirality switching; Ketimine; Stereoselective crystallization;; Binaphthoic acid
摘要：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.