Self-disproportionation of Enantiomers (SDE) of Chiral Nonracemic Amides via Achiral Chromatography

This article is based on a review of literature devoted to the phenomenon of SDE via achiral chromatography since the appearance of the seminal work of Professor Emanuel Gil-Av. The discussed examples of chromatographic studies are related to amides derived from chiral amines and alpha- and beta-amino acids. We discuss the observed SDE magnitude as a function of a compound's structure, and composition of eluent and stationary phases, providing some mechanistic considerations. Particular emphasis is given to the aspect of SDE via achiral chromatography as an emerging unconventional enantiomeric purification technique.