Deracemization in a Complex Quaternary System with a Second-Order Asymmetric Transformation by Using Phase Diagram Studies |
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| Authors: | Ryusei Oketani Francesco Marin Dr Paul Tinnemans Marine Hoquante Anne Laurent Dr Clément Brandel Prof Dr Pascal Cardinael Dr Hugo Meekes Prof Dr Elias Vlieg Prof Dr Yves Geerts Prof Dr Gérard Coquerel |
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| Institution: | 1. UFR des Sciences et Techniques, Laboratoire SMS-EA3233, Université de Rouen Normandie, Place Emile Blondel, 76821 Mont-Saint-Aignan, France;2. Laboratoire de Chimie des Polymères, Faculté des Sciences, Université libre de Bruxelles (ULB), Boulevard du Triomphe, 1050 Brussels, Belgium;3. Radboud University, Institute for Molecules and Materials, Heyendaalseweg 135, 6525 AJ, Nijmegen, The Netherlands |
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| 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. |
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| Keywords: | atropisomerism chiral resolution deracemization phase diagrams second-order asymmetric transformation |
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