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- Title
Deracemization in a Complex Quaternary System with a Second‐Order Asymmetric Transformation by Using Phase Diagram Studies.
- Authors
Oketani, Ryusei; Marin, Francesco; Tinnemans, Paul; Hoquante, Marine; Laurent, Anne; Brandel, Clément; Cardinael, Pascal; Meekes, Hugo; Vlieg, Elias; Geerts, Yves; Coquerel, Gérard
- Abstract
A productive deracemization process based on a quaternary phase diagram study of a naphthamide derivative is reported. New racemic compounds of an atropisomeric naphthamide derivative have been discovered, and a quaternary phase diagram has been constructed that indicated that four solids are stable in a methanol/H2O solution. Based on the results of a heterogeneous equilibria study showing the stable domain of the conglomerate, a second‐order asymmetric transformation was achieved with up to 97 % ee. Furthermore, this methodology showcases the chiral separation of a stable racemic compound forming system and does not suffer from any of the typical limitations of deracemization, although application is still limited to conglomerate‐forming systems. We anticipate that this present study will serve as a fundamental model for the design of sophisticated chiral separation processes.
- Subjects
DERACEMIZATION; PHASE diagrams; RACEMIC mixtures; RESOLUTION (Chemistry); CONGLOMERATE
- Publication
Chemistry - A European Journal, 2019, Vol 25, Issue 61, p13890
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201903338