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Simultaneously resolving BINOL and proline using a stoichiometric cocrystal switch

Songsermsawad, Sarita;Shemchuk, Oleksii;Robeyns, Koen;Collard, Laurent;Leyssens, Tom;et.al.
(2024) Chemical Communications — (2024)

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We here highlight the importance of stoichiometry for simultaneous cocrystal resolution. Focusing on combining the racemates of binol and proline, we show that a 1 : 2 ratio leads to formation of a full racemic compound, whereas a 2 : 1 ratio, leads to conglomerate formation, with simultaneous resolution of both binol and proline. Playing on stoichiometry, one achieves a reversible switch between the racemic compound and conglomerate. This is the first investigation of such behavior combining two racemates.
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Songsermsawad, S., Shemchuk, O., Robeyns, K., Collard, L., E. Flood, A., & Leyssens, T. (2024). Simultaneously resolving BINOL and proline using a stoichiometric cocrystal switch. Chemical Communications. Published. https://doi.org/10.1039/d4cc02180k (Original work published 2024)