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

Mayaka Maeno, Etsuko Tokunaga, Takeshi Yamamoto, Toshiya Suzuki, Yoshiyuki Ogino, Emi Ito, Motoo Shiro, Toru Asahi, Norio Shibata

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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.

    Original languageEnglish
    Pages (from-to)1043-1048
    Number of pages6
    JournalChemical Science
    Issue number2
    Publication statusPublished - 2015 Feb 1


    ASJC Scopus subject areas

    • Chemistry(all)

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