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Practical aspects on how to deracemize atropizomers by means of crystallization

Abstract : Chiral separation techniques are important for enabling studies relating to the biological functions and activities of chiral molecules. In this thesis, chiral separations by deracemization, an approach that combines racemization with crystallization, have been studied from the practical and theoretical viewpoints using atropisomeric naphthamide In Chapter 2, we studied the first experimental proof of the impact of racemization kinetics on global temperature cycle induced deracemization (TCID) kinetics as well as on process productivity. The racemization kinetics are linearly related to the global TCID kinetics, and the process productivity was related not only to the racemization kinetics but also to the solubility of the compound. In Chapter3, we performed a comparison study of process productivities of TCID and second-order asymmetric transformation (SOAT). We demonstrated that the process productivity of TCID is independent of the scale of the system. Then, we found that SOAT is a productive process, while TCID gives highly enantiopure products. In Chapter 4, a problematic case of the deracemization of a single compound forming multiple solid phases was demonstrated using a phase diagram study. Although racemization adds complexity to the phase diagram, we sought to show the construction of a phase diagram for racemizable compounds and how the diagram enabling deracemization.
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Ryusei Oketani. Practical aspects on how to deracemize atropizomers by means of crystallization. Organic chemistry. Normandie Université, 2019. English. ⟨NNT : 2019NORMR109⟩. ⟨tel-02502796⟩



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