98184-94-2Relevant academic research and scientific papers
NAD(P)H MODELS 20 CHEMOSELECTIVE METAL ION CATALYZED REDUCTION OF α-KETO-β,γ-UNSATURATED ESTERS BY 1,4-DIHYDROPYRIDINE DERIVATIVES
Meijer, Louis H. P.,Pandit, Upendra K.
, p. 467 - 472 (1985)
Ethyl 2-oxo-4-aryl-3-butene-1-oates (1a-c) are reduced by NAD(P)H models (1-n-propyl-1,4-dihydronicotinamide (4) and Hantzsch ester (5)), in presence of magnesium perchlorate.One equivalent of the reductant reduces the substrates selectively to the corresponding 2-oxo-4-arylbutanoates (6, 10a, b).An additional equivalent and higher temperature, converts ethyl 2-oxo-4-phenylbutanoate (6) to ethyl 2-hydroxy-4-phenylbutanoate (7).Reduction of ethyl 2-oxo-4-phenyl-3-buten-1-oate (1a) by Hantzsch ester in C2H5OD or by Hantzsch ester-4,4-d2 in C2H5OH, leads to direct transfer of the hydrogen or deuterium, respectively, without isotopic scrambling.These results have been interpreted to support the hydride transfer mechanism.
