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Deracemization in a Complex Quaternary System with a Second‐Order Asymmetric Transformation by Using Phase Diagram Studies
Author(s) -
Oketani Ryusei,
Marin Francesco,
Tinnemans Paul,
Hoquante Marine,
Laurent Anne,
Brandel Clément,
Cardinael Pascal,
Meekes Hugo,
Vlieg Elias,
Geerts Yves,
Coquerel Gérard
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201903338
Subject(s) - phase diagram , transformation (genetics) , derivative (finance) , domain (mathematical analysis) , phase (matter) , diagram , quaternary , materials science , combinatorial chemistry , mathematics , chemistry , organic chemistry , geology , mathematical analysis , paleontology , statistics , financial economics , economics , gene , biochemistry
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/H 2 O 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.