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Cocrystallization‐Induced Spontaneous Deracemization: A General Thermodynamic Approach to Deracemization
Author(s) -
Guillot Michael,
Meester Joséphine,
Huynen Sarah,
Collard Laurent,
Robeyns Koen,
Riant Olivier,
Leyssens Tom
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202002464
Subject(s) - context (archaeology) , chemistry , enantiomer , diastereomer , crystallization , limiting , combinatorial chemistry , organic chemistry , biology , mechanical engineering , paleontology , engineering
Processes leading to enantiomerically pure compounds are of utmost importance, in particular for the pharmaceutical industry. Starting from a racemic mixture, crystallization‐induced diastereomeric transformation allows in theory for 100 % transformation of the desired enantiomer. However, this method has the inherent limiting requirement for the organic compound to form a salt. Herein, this limitation is lifted by introducing cocrystallization in the context of thermodynamic deracemization, with the process applied to a model chiral fungicide. We report a new general single thermodynamic deracemization process based on cocrystallization for the deracemization of ( R , S )‐4,4‐dimethyl‐1‐(4‐fluorophenyl)‐2‐(1 H ‐1,2,4‐triazol‐1‐yl)pentan‐3‐one. This study demonstrates the feasibility of this novel approach and paves the way to further development of such processes.