Non-superimposable mirror image crystals of enantiomers by spontaneous resolution and the chiral discrimination mechanism

Non-superimposable mirror image crystals of both enantiomers (S/R) of cyclic γ-alkenyl alcohol (2) have been recognized and remarkably identified by the naked eye. More interestingly, both crystals are an outcome of most astonishingly H-bond and intermolecular σ/π–π interactions. They accounted for the relatively rare and less predictable spontaneous resolution with optical purity >99% ee from the racemic mixture. The chiral discrimination mechanism of this spontaneous resolution has also been proposed.

Graphical abstractNon-superimposable mirror image crystals of both enantiomers (S/R) are an outcome of the most astonishingly H-bond and intermolecular σ/π–π interactions which can account for the relatively rare and less predictable spontaneous resolution.Figure optionsDownload full-size imageDownload as PowerPoint slide