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

Organic Letters
Frank T JereJames E Jackson

Abstract

[reaction: see text] At 100 degrees 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 alpha-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.

Citations

Apr 4, 2017·Chemical Communications : Chem Comm·Jasper Verduyckt, Dirk E De Vos
Sep 16, 2015·Angewandte Chemie·Céline TaglangGrégory Pieters
Apr 26, 2018·Journal of Motor Behavior·D Adam Quirk, Cheryl L Hubley-Kozey
May 16, 2014·Chemical Communications : Chem Comm·Masazumi TamuraKeiichi Tomishige

Related Concepts

Amino Alcohols
Catalysis
Deuterons
Hydrogenation
Solutions
Molecular Stereochemistry

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