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We have discovered the first case of accomplishment of an enantiomeric resolution by simple recrystallization of a series of racemic compounds [(±) forms] composed of a regular packing of (+) and (-) molecules in a crystal, although in principle this sort of enantiomeric resolution has been considered to be infeasible for more than a century since the discovery of chiral crystals by Pasteur and preferential crystallization of conglomerates by Gernetz which are a mixture of homochiral (+) and (-) crystals. We have designated this new enantiomeric resolution phenomenon as “Preferential Enrichment”. Here we report a distinct evidence that polymorphism between a racemic compound and a mixed crystal (solid solution), which consists of alternating alignment of the two homochiral dimers in a crystal, is responsible for the “Preferential Enrichment”, and we propose a mechanism of the phenomenon of the reversal of chirality in the deposited crystals, that is the essence of the “Preferential Enrichment”, on the basis of the polymorphic transformation during crystallization.

New Enantiomeric Resolution Phenomenon of Racemic Crystals : Preferential Enrichment