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

    Research output: Contribution to journalArticle

    26 Citations (Scopus)

    Abstract

    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
    Volume6
    Issue number2
    DOIs
    Publication statusPublished - 2015 Feb 1

    Fingerprint

    Thalidomide
    Enantiomers
    Silica Gel
    Chromatography
    Gravitation
    Fluorine
    Atoms
    3-fluorothalidomide

    ASJC Scopus subject areas

    • Chemistry(all)

    Cite this

    Self-disproportionation of enantiomers of thalidomide and its fluorinated analogue via gravity-driven achiral chromatography : Mechanistic rationale and implications. / Maeno, Mayaka; Tokunaga, Etsuko; Yamamoto, Takeshi; Suzuki, Toshiya; Ogino, Yoshiyuki; Ito, Emi; Shiro, Motoo; Asahi, Toru; Shibata, Norio.

    In: Chemical Science, Vol. 6, No. 2, 01.02.2015, p. 1043-1048.

    Research output: Contribution to journalArticle

    Maeno, Mayaka ; Tokunaga, Etsuko ; Yamamoto, Takeshi ; Suzuki, Toshiya ; Ogino, Yoshiyuki ; Ito, Emi ; Shiro, Motoo ; Asahi, Toru ; Shibata, Norio. / Self-disproportionation of enantiomers of thalidomide and its fluorinated analogue via gravity-driven achiral chromatography : Mechanistic rationale and implications. In: Chemical Science. 2015 ; Vol. 6, No. 2. pp. 1043-1048.
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