Abstract

Preferential enrichment is an unusual symmetry-breaking enantiomeric resolution phenomenon that is initiated by the solvent-assisted solid-to-solid transformation of a metastable polymorphic form into a thermodynamically stable one during crystallization from the supersaturated solution of a certain kind of racemic crystals. On the basis of the proposed mechanism of preferential enrichment, both induction and inhibition of preferential enrichment were successfully achieved by controlling the mode of the polymorphic transition during crystallization either by minor molecular modification or with appropriate seed crystals. Furthermore, by inducing a desired polymorphic transition during crystallization of several α-amino acids or their cocrystals with dicarboxylic acids, which were classified as a racemic compound, preferential enrichment could also be accomplished.

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