Synthesis of chiral 2-indolyl methanamines and insight into the stereochemistry protecting effects of the 9-phenyl-9-fluorenyl protecting group

C.S. Lood, A.E. Laine, A. Högnäsbacka, M. Nieger, A.M.P Koskinen

    Tutkimustuotos: LehtiartikkeliArticleScientificvertaisarvioitu

    5 Sitaatiot (Scopus)
    158 Lataukset (Pure)

    Abstrakti

    Tetrahydro-β-carbolines, a privileged structural feature in natural products and pharmaceutically active compounds, has been the cause for considerable research interest, spanning many decades. Herein is reported the synthesis of
    the structurally closely related compounds denoted as (indol-2-yl)methanamines, in 99% ee using amino acid starting materials, coupled with a 9-phenyl-9-fluorenyl (Pf) protecting group strategy. Furthermore a conformational study of Pfprotected α-amino carbonyl compounds were undertaken by means of DFT refined molecular mechanics calculation, Xray crystallography measurements and NMR experiments in
    order to elucidate the stereochemical protecting properties induced by the Pf group.
    AlkuperäiskieliEnglanti
    Sivut3793-3805
    JulkaisuEuropean Journal of Organic Chemistry
    Vuosikerta2015
    Numero17
    DOI - pysyväislinkit
    TilaJulkaistu - 2015
    OKM-julkaisutyyppiA1 Julkaistu artikkeli, soviteltu

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