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Photochemical Deracemization of a Medicinally‐Relevant Benzopyran using an Oscillatory Flow Reactor
Author(s) -
Williams Jason D.,
Pöchlauer Peter,
Okumura Yoshiyuki,
Inami Yukari,
Kappe C. Oliver
Publication year - 2022
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.202200741
Subject(s) - racemization , diastereomer , crystallization , yield (engineering) , chemistry , biological system , combinatorial chemistry , biochemical engineering , materials science , organic chemistry , engineering , metallurgy , biology
Dynamic deracemization processes, such as crystallization‐induced diastereomer transformations (CIDTs), offer the opportunity to combine racemization and resolution processes, to provide high yields of enantiomerically pure compounds. To date, few of these processes have incorporated photochemical racemization. By combining batch crystallization with a flow photoreactor for efficient irradiation, it is possible to perform such deracemization in an effective, scalable and high yielding manner. After applying design of experiment (DoE) principles and mathematical modelling, the most efficient parameter set could be identified, leading to excellent results in just 4 h reaction time: isolated yield of 82 % and assay ee of 96 %. Such photochemical racemization methods can serve to open new avenues for preparation of enantiomerically pure functional molecules on both small and industrially‐relevant scales.