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

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    Abstract

    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.
    Original languageEnglish
    Pages (from-to)3793-3805
    JournalEuropean Journal of Organic Chemistry
    Volume2015
    Issue number17
    DOIs
    Publication statusPublished - 2015
    MoE publication typeA1 Journal article-refereed

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