Self-disproportionation of enantiomers of thalidomide and its fluorinated analogue gravity-driven achiral chromatography: mechanistic rationale and implications.

We report on the self-disproportionation of enantiomers (SDE) of non-racemic thalidomide () and 3'-fluorothalidomide () under the conditions of gravity-driven achiral silica-gel chromatography. The presence of a fluorine atom on the chiral center dramatically alters the structure and polarity of and , resulting in the opposite SDE profile on silica-gel.