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

Abstract

We report on the self-disproportionation of enantiomers (SDE) of non-racemic thalidomide (<b>1</b>) and 3'-fluorothalidomide (<b>2</b>) 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 <b>1</b> and <b>2</b>, resulting in the opposite SDE profile on silica-gel.