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

chemical science

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