Separation of a diastereomeric diol pair using the mechanical properties of crystals

Abstract

We report the separation of a (2S,3R/S)-3-ethyl-1-phenylhex-5-ene-2,3-diol (ephd) diastereomeric pair with visually indistinguishable acicular morphologies based on their mechanical responses, which is found to be more efficient than conventional separation methods. Furthermore, the molecular crystals of (2S,3R)-ephdshow elastic deformation, while (2S,3S)-ephdfractures in a brittle manner under similar conditions.