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

    Research output: Contribution to journalArticle

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    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.

    Original languageEnglish (US)
    Pages (from-to)527-530
    Number of pages4
    JournalOrganic Letters
    Volume5
    Issue number4
    DOIs
    StatePublished - Feb 20 2003

    Profile

    activation
    acids
    Amino Alcohols
    Hydrogenation
    Amino Acids
    Acids
    Cape Verde
    alanine
    hydrogenation
    catalysts
    hydrogen
    Alanine
    Hydrogen
    Afferent Loop Syndrome
    Deoxyribonucleoproteins
    stereochemistry
    carboxylates
    amino acids
    deuterium
    alcohols

    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: Contribution to journalArticle

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

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

    Research output: Contribution to journalArticle

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