Remarkable Amplification of the Self‐Disproportionation of Enantiomers on Achiral‐Phase Chromatography Columns

A phase they're going through: The enantiomers of chiral compounds containing a trifluoromethyl group directly bonded to a stereogenic carbon center are prone to self-disproportionation on columns of achiral silica gel (see picture). Thus, all fluorine-containing chiral reagents and drugs, as well as literature data on the stereochemical outcome of asymmetric transformations involving fluorine-containing compounds, should be reevaluated.