Stereoretentive C-H bond activation in the aqueous phase catalytic hydrogenation of amino acids to amino alcohols

    Research output: Research - peer-reviewArticle

    • 28 Citations

    Abstract

    (Matrix presented) At 100°C and 1000 psi of hydrogen, aqueous L-alanine undergoes facile hydrogenation to L-alaninol over a 5% Ru/C catalyst. In the presence of added acid to protonate the carboxylate moiety, the reaction is faster and more selective than analogous reductions of simple alkanoic acids. Stereochemistry at the α-carbon is retained despite complete exchange of hydrogen at this site, as shown by deuterium incorporation. Similar stereoretentive C-H bond activation at C2 is seen in L-alaninol itself, and when acid is omitted, in L-alanine. These processes reveal a class of mild, highly stereoretentive C-H bond activations occurring in water over a heterogeneous catalyst.

    LanguageEnglish (US)
    Pages527-530
    Number of pages4
    JournalOrganic Letters
    Volume5
    Issue number4
    DOIs
    StatePublished - Feb 20 2003

    Profile

    Amino Alcohols
    Alanine
    Hydrogenation
    Hydrogen
    Chemical activation
    Amino Acids
    Catalysts
    Acids
    2-aminopropanol
    hydrogenation
    amino acids
    alcohols
    activation
    acids
    alanine
    catalysts
    hydrogen
    Stereochemistry
    Deuterium
    Carboxylic acids

    ASJC Scopus subject areas

    • Molecular Medicine

    Cite this

    Stereoretentive C-H bond activation in the aqueous phase catalytic hydrogenation of amino acids to amino alcohols. / Jere, Frank T.; Miller, Dennis J.; Jackson, James E.

    In: Organic Letters, Vol. 5, No. 4, 20.02.2003, p. 527-530.

    Research output: Research - peer-reviewArticle

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