170564-98-4Relevant articles and documents
Chiral Lewis Base-Catalyzed, Enantioselective Reduction of Unprotected β-Enamino Esters with Trichlorosilane
Ye, Jianheng,Wang, Chao,Chen, Lin,Wu, Xinjun,Zhou, Li,Sun, Jian
supporting information, p. 1042 - 1047 (2016/04/19)
Catalytic asymmetric reduction of N-unsubstituted β-enamino esters represents a major challenge for asymmetric catalysis. In this paper, the first organocatalytic system that could be used for the asymmetric hydrosilylation of N-unsubstituted β-enamino esters has been developed. Using N-tert-butylsulfinyl-L-proline-derived amides and L-pipecolinic acid-derived formamides as catalyst, a broad range of β-aryl- and β-alkyl-substituted free β-amino esters could be prepared with high yields and enantioselectivities. The practicality was illustrated by the gram-scale asymmetric synthesis of ethyl (R)-3-amino-3-phenylpropanoate and isopropyl (S)-3-amino-4-(2,3,5-trifluorophenyl)butanoate. The resulting product can be smoothly transformed to the FDA approved medicines dapoxetine and sitagliptin in a short synthetic route.
PROCESS FOR THE SAFE OZONOLYSIS OF ORGANIC COMPOUNDS IN FLAMMABLE SOLVENTS
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Page/Page column 22, (2008/12/06)
An improved process for the safe ozonolysis of unsaturated, organic carbon compounds having one or more olefinic or aromatic double bonds in the molecule in flammable solvents for the preparation of mono- or biscarbonyl or hydroxy compounds, in which ozonolysis is carried out with the use of an ozone-carrying inert gas/O2 stream, in which the oxygen concentration in the inert gas/O2 stream is above the known limiting oxygen concentration of the homogeneous fuel/gas mixtures and below the safety-critical limiting oxygen concentration of the heterogeneous mixture of the liquid fuel and oxygen-containing gas which is dependent on the reaction conditions and at which ignition and flame propagation no longer take place.
Preparation of enantiomerically pure (R)- and (S)-3-amino-3-phenyl-1- propanol via resolution with immobilized penicillin G acylase
Fadnavis, Nitin W.,Radhika, Kasiraman R.,Vedamayee Devi
, p. 240 - 244 (2007/10/03)
Ethyl 2,4-dioxo-4-phenylbutyrate, obtained by condensation of acetophenone with diethyl oxalate, was converted to 3-oxo-3-phenyl-1-propanol in 90% yield by reaction with baker's yeast. Reductive amination with sodium cyanoborohydride in the presence of ammonium acetate gave the racemic 3-amino-3-phenyl-1-propanol in 65% yield. Enzymatic resolution of the corresponding N-phenylacetyl derivative with penicillin G acylase, immobilized on an epoxy resin gave (S)-amide and (R)-amino alcohol in high enantiomeric purity (ee >99%) and >45% yields for each enantiomer.