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Chirality Switching in the Crystallization of 1‐(4‐Chlorophenyl)ethylamine with Binaphthoic Acid by Ketimine Formation
Author(s) -
Jin YingJi,
Choi Yunseo,
Chen Qian,
Shirbhate Mukesh Eknath,
Huang Haofei,
Kim Youngmee,
Kim SungJin,
Jun MooJin,
Koo Eon Cheol,
Kim Kwan Mook
Publication year - 2016
Publication title -
bulletin of the korean chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.237
H-Index - 59
ISSN - 1229-5949
DOI - 10.1002/bkcs.10929
Subject(s) - ethylamine , diastereomer , imine , chirality (physics) , chemistry , crystallization , stereochemistry , crystallography , organic chemistry , catalysis , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
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.