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Abstract
Described is a new strategy using cocrystallization, one of the crystal engineering techniques, to convert a racemic compound crystal into a racemic mixed crystal which can show preferential enrichment, a symmetry-breaking spontaneous enantiomeric resolution phenomenon observed upon recrystallization of a certain kind of racemic mixed crystal with a fairly ordered arrangement of the two enantiomers under nonequilibrium conditions. The 1:1 cocrystal (2) of (dl)-phenylalanine (Phe) and fumaric acid satisfied the requirements proposed for the occurrence of preferential enrichment, such as (i) a sufficient solubility difference (racemic crystal ≪ enantiomeric crystal), (ii) the occurrence of polymorphic transition during crystallization, and (iii) the deposition of nonracemic mixed crystals with a unique crystal structure, and thus successfully showed preferential enrichment. In contrast, a racemic compound (dl)-Phe itself failed to show a polymorphic transition during crystallization and thereby preferential...
Published Version
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