A practical access to highly enantiomerically pure flavanones by catalytic asymmetric transfer hydrogenation

Marie Kristin Lemke, Pia Schwab, Petra Fischer, Sandra Tischer, Morris Witt, Laurence Noehringer, Victor Rogachev, Anne Jäger, Olga Kataeva, Roland Fröhlich, Peter Metz

    Research output: Contribution to journalArticle

    28 Citations (Scopus)

    Abstract

    A surprisingly selective, non-enzymatic kinetic resolution of readily available, racemic β-chiral ketones enabled the title process, which was applied to a rapid synthesis of several bioactive flavanones in virtually enantiopure form (see scheme; MOM=methoxymethyl, Ts=p-toluenesulfonyl).

    Original languageEnglish
    Pages (from-to)11651-11655
    Number of pages5
    JournalAngewandte Chemie - International Edition
    Volume52
    Issue number44
    DOIs
    Publication statusPublished - 25 Oct 2013

    Fingerprint

    Flavanones
    Ketones
    Hydrogenation
    Kinetics

    Keywords

    • asymmetric catalysis
    • flavonoids
    • glabrol
    • kinetic resolution
    • natural products

    ASJC Scopus subject areas

    • Catalysis
    • Chemistry(all)

    Cite this

    A practical access to highly enantiomerically pure flavanones by catalytic asymmetric transfer hydrogenation. / Lemke, Marie Kristin; Schwab, Pia; Fischer, Petra; Tischer, Sandra; Witt, Morris; Noehringer, Laurence; Rogachev, Victor; Jäger, Anne; Kataeva, Olga; Fröhlich, Roland; Metz, Peter.

    In: Angewandte Chemie - International Edition, Vol. 52, No. 44, 25.10.2013, p. 11651-11655.

    Research output: Contribution to journalArticle

    Lemke, MK, Schwab, P, Fischer, P, Tischer, S, Witt, M, Noehringer, L, Rogachev, V, Jäger, A, Kataeva, O, Fröhlich, R & Metz, P 2013, 'A practical access to highly enantiomerically pure flavanones by catalytic asymmetric transfer hydrogenation', Angewandte Chemie - International Edition, vol. 52, no. 44, pp. 11651-11655. https://doi.org/10.1002/anie.201306500
    Lemke, Marie Kristin ; Schwab, Pia ; Fischer, Petra ; Tischer, Sandra ; Witt, Morris ; Noehringer, Laurence ; Rogachev, Victor ; Jäger, Anne ; Kataeva, Olga ; Fröhlich, Roland ; Metz, Peter. / A practical access to highly enantiomerically pure flavanones by catalytic asymmetric transfer hydrogenation. In: Angewandte Chemie - International Edition. 2013 ; Vol. 52, No. 44. pp. 11651-11655.
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