88768-19-8Relevant academic research and scientific papers
Catalytic cyclization reactions of Huisgen zwitterion with -ketoesters by in situ chemoselective phosphine oxide reduction
Fourmy, Kévin,Voituriez, Arnaud
supporting information, p. 1537 - 1540 (2015/03/30)
The first examples of catalytic cyclization reactions between the Huisgen zwitterion and α-ketoester derivatives are reported. The use of phenylsilane with a substoichiometric amount of bis(p-nitrophenyl)phosphate/diisopropylethylamine proved to be crucial for the in situ reduction of the phosphine oxide formed during the reaction. The optimized protocol is applied to alkyl or aryl ketoesters, furnishing either the corresponding cycloadducts or the hydrazone derivatives, depending on the substitution patterns of the substrates, in moderate to good yields (up to 80% yield, 18 examples).
Highly enantioselective hydrogenation of 2-oxo-4-arybutanoic acids to 2-hydroxy-4-arylbutanoic acids
Zhu, Lufeng,Chen, Houhe,Meng, Qinghua,Fan, Weizheng,Xie, Xiaomin,Zhang, Zhaoguo
supporting information; experimental part, p. 6186 - 6190 (2011/09/19)
The Ru-catalyzed asymmetric hydrogenation of 2-oxo-4-arybutanoic acids to afford 2-hydroxy-4-arybutanoic acids was accomplished by employing SunPhos as chiral ligand and 1 M aq HBr as additive. The high enantioselectivities (88.4%-92.6% ee) and efficiency (TON=10,000, TOF=300 h-1) make this method efficient for the synthesis of an important intermediate, (R)-2-hydroxy-4-phenylbutanoic acid, for ACE inhibitors.
Stereochemical control in microbial reduction. Part 31: Reduction of alkyl 2-oxo-4-arylbutyrates by baker's yeast under selected reaction conditions
Dao, Duc Hai,Okamura, Mutsuo,Akasaka, Takeshi,Kawai, Yasushi,Hida, Kouichi,Ohno, Atsuyoshi
, p. 2725 - 2737 (2007/10/03)
Treatment of baker's yeast with phenacyl chloride in an aqueous-organic solvent has been proven to be an effective method of inhibiting the enzymes that afford (S)-enantiomers of α-hydroxy esters in the reduction of α-keto esters. The procedure is effective for the whole-cell system to produce the (R)-product with high chemical yield and high enantiomeric excess.
Practical Enantioselective Synthesis of a Homotyrosine Derivative and (R,R)-4-Propyl-9-hydroxynaphthoxazine, a Potent Dopamine Agonist
Melillo, David G.,Larsen, Robert D.,Mathre, David J.,Shukis, William F.,Wood, Alfred W.,Colleluori, Joseph R.
, p. 5143 - 5150 (2007/10/02)
Two enantioselective routes were developed to prepare chiral amino acid derivative 4.The key step in the first route was catalytic hydrogenation of acrylate derivative 3 using chiral rhodium catalysts.In the second route the key step was acylation of 2-ch
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 (2007/10/02)
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.
