Synthesis of Enantiopure Benzyl Homoallylamines by Indium-Mediated Barbier-Type Allylation Combined with Enzymatic Kinetic Resolution: Towards the Chemoenzymatic Synthesis of N-Containing Heterocycles

Ari Hietanen, Tiina Saloranta, Sara Rosenberg, Evelina Laitinen, Reko Leino, Liisa T. Kanerva

    Research output: Contribution to journalArticleScientificpeer-review

    18 Citations (Scopus)

    Abstract

    Barbier-type indium-mediated allylations of different N,N(dimethylsulfamoyl)-protected aldimines with a number of allyl bromides followed by high-yielding deprotection afforded allylic amines in good to excellent yields. The racemic amines were then subjected to enzymatic kinetic resolution in order to obtain the corresponding (S)-amines and (R)-amides. When acyl donors with a terminal double bond were applied in the enzymatic kinetic resolution, the product amide could be converted into unsaturated lactams in a straightforward manner by utilizing ring-closing metathesis. Furthermore, the enantiopure (S)-1-phenylbut-3-enylamine was converted into the corresponding diallylamine, which was subjected to ring-closing metathesis to yield a substituted dehydropiperidine mimicking a number of natural products.
    Original languageUndefined/Unknown
    Pages (from-to)909–919
    Number of pages11
    JournalEuropean Journal of Organic Chemistry
    Volume2010
    Issue number5
    DOIs
    Publication statusPublished - 2010
    MoE publication typeA1 Journal article-refereed

    Keywords

    • Allylation
    • Amines
    • Enzyme catalysis
    • Kinetic resolution
    • Ring-closing metathesis

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