Self-disproportionation of enantiomers (SDE) of chiral sulfur-containing compounds via achiral chromatography

Abstract

This review presents a comprehensive, critical treatment of all the literature data related to the phenomenon of the SDE taking place during gravity-driven achiral chromatography of scalemic compounds bearing sulfoxide and thioamide functionalities. The discussion is focused on the SDE magnitude as a function of the structure iof the compound, composition of eluent and stationary phase, including some mechanistic details. An apparent possibility of application of the SDE phenomenon via achiral chromatography as a novel, emerging unconventional enantiomeric purification technique is also discussed. O S Tol-p Me achiral column chromatography 86.0%