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.

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

Profile

Amino Alcohols
Hydrogenation
Alanine
hydrogenation
amino acids
Hydrogen
alcohols
Chemical activation
activation
alanine
Amino Acids
acids
Stereochemistry
Catalysts
Acids
Deuterium
Carboxylic acids
catalysts
Carbon
stereochemistry

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

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