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  • 1.
    Bogár, Krisztián
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Olofsson, Berit
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Fransson, Ann-Britt L.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Asymmetric synthesis of 3,5-disubstituted piperidines by enzyme-metal combo catalysis2006In: Enzymatic Synthesis, Stockholm, Sweden, 2006Conference paper (Other (popular science, discussion, etc.))
  • 2.
    Olofsson, Berit
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bogár, Krisztián
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Fransson, Ann-Britt L
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Divergent asymmetric synthesis of 3,5-disubstituted piperidines.2006In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 71, no 21, p. 8256-60Article in journal (Refereed)
    Abstract [en]

    A divergent synthesis of various 3,5-dioxygenated piperidines with interesting pharmacological properties is described. A mixture of the achiral cis- and racemic trans-3,5-piperidine diol could be efficiently obtained from N-benzylglycinate in five steps by the use of chemoenzymatic methods. In the subsequent enzyme- and Ru-catalyzed reaction, the rac/meso diol mixture was efficiently transformed to the cis-(3R,5S)-diacetate with excellent diastereoselectivity and in high yield. Further transformations of the cis-diacetate selectively delivered the cis-piperidine diol and the cis-(3R,5S)-hydroxy acetate. Alternatively, the DYKAT could be stopped at the monoacetate stage to give the trans-(3R,5R)-hydroxy acetate.

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