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

被引:47
|
作者
Jere, FT
Miller, DJ
Jackson, JE [1 ]
机构
[1] Michigan State Univ, Dept Chem Engn & Mat Sci, E Lansing, MI 48824 USA
[2] Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA
关键词
D O I
10.1021/ol0274211
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] At 100 degreesC 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.
引用
收藏
页码:527 / 530
页数:4
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