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141.
Meryem Fistikci Ozlem Gundogdu Derya Aktas Hasan Secen M. Fethi Sahin Ramazan Altundas Yunus Kara 《Tetrahedron》2012,68(12):2607-2610
A new synthetic strategy for (R)- and (S)-3-hydroxy-4-(2,4,5-trifluorophenyl)butanoic acid, a building block in the preparation of sitagliptin and its derivatives, was developed. Pd(OAc)2 catalyzed coupling of 2,4,5-trifluoro-1-iodobenzene with allyl alcohol gave 3-(2,4,5-trifluorophenyl)propanal in a yield of 95%. l-Proline catalyzed reaction of the 3-phenylpropanal (in only 1.2 molar equiv) with nitrosobenzene followed by reduction with NaBH4 and Pd/C catalyzed hydrogenation gave (R)-3-(2,4,5-trifluorophenyl)propane-1,2-diol with >99% ee and 65% yield. Selective tosylation of primary hydroxyl group of the 1,2-propandiol unit followed by cyanide displacement afforded (R)-3-hydroxy-4-(2,4,5-trifluorophenyl)butanenitrile (80%). The nitrile was converted to the title β-hydroxy acid under basic hydrolysis in a yield of 90%. Thus, (R)-3-hydroxy-4-(2,4,5-trifluorophenyl)butanoic acid was prepared enantioselectively from the starting material in four steps and 45% overall yield. The reaction sequence was repeated with d-proline as the catalyst to give (S)-3-hydroxy-4-(2,4,5-trifluorophenyl)butanoic acid in 45% overall yield and >99% enantiomeric excess. 相似文献
142.
In this study, the sorption behavior of two important contaminants, phenol and radioactive cesium (137Cs), onto surfactant modified insolubilized humic acid (SMIA) were investigated as a function of time, sorbate concentration
utilizing the radiotracer method and UV–Vis spectroscopy. Phenol sorption process was well described by both Freundlich and
Tempkin type isotherms, and cesium sorption was described by Freundlich and Dubinin–Radushkevich isotherms. It was found that
SMIA adsorbs both cations and phenolic substances. Kinetic studies indicated that adsorption behavior of phenol obey the pseudo
second order rate law. FTIR spectroscopic technique was used to understand the structural changes during modification process
with surfactants. 相似文献