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Simultaneous Chiral Resolution of Two Racemic Compounds by Preferential Cocrystallization **
Author(s) -
Zhou Fuli,
Shemchuk Oleksii,
Charpentier Maxime D.,
Matheys Chloé,
Collard Laurent,
ter Horst Joop H.,
Leyssens Tom
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202107804
Subject(s) - mandelic acid , enantiomer , crystallization , chiral resolution , chemistry , resolution (logic) , stereochemistry , combinatorial chemistry , kinetic resolution , enantiomeric excess , enantioselective synthesis , organic chemistry , catalysis , artificial intelligence , computer science
We tap into an unexplored area of preferential crystallization, being the first to develop simultaneous chiral resolution of two racemic compounds by preferential cocrystallization. We highlight how the two racemic compounds RS ‐mandelic acid (MAN) and RS ‐etiracetam (ETI) can be combined together as enantiospecific R‐MAN⋅R‐ETI and S‐MAN⋅S‐ETI cocrystals forming a stable conglomerate system and subsequently develop a cyclic preferential crystallization allowing to simultaneous resolve both compounds . The developed process leads to excellent enantiopurity both for etiracetam ( ee >98 %) and mandelic acid ( ee ≈95 %) enantiomers.