The first example of a macrocyclic lariat-type compound 3, which, despite being achiral in solution, undergoes asymmetric crystallization and enantiomeric excess, was observed for a sample of ground crystals. Among 32 independent crystallizations, in 23 cases of samples an enantiomeric excess was observed; furthermore six of these included a vast majority of one enantiomer.
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Kalisiak et al. (2005) studied this question.
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