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Stereoretentive C−H Bond Activation in the Aqueous Phase Catalytic Hydrogenation of Amino Acids to Amino Alcohols

2003; American Chemical Society; Volume: 5; Issue: 4 Linguagem: Inglês

10.1021/ol0274211

1523-7060

Frank T. Jere, Dennis J. Miller, James E. Jackson,

Asymmetric Synthesis and Catalysis

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.