Synthesis And Application In Chiral Recognition And Catalysis Of The New Chiral Amino Alcohols

Chiral solvating agent(CSA) for NMR can detect the enantiomeric purity of racemic chiral acid compounds which cause biochemical behavior simply and directly. This method can be simply operated, and it’s application in testing enantiomeric purity and configuration of chiral compounds is getting mature. Among all chiral solvating agents and catalysts, chiral amino alcohols are widly used. Whereas, few research about their use in identification of chiral acid compounds are published. Thus, it’s important trying to synthetise chiral amino alcohols that can be more effectively used in the identification of chiral acids, based on known research.(1). Bidentate chiral amino alcohols (2S)-2-amino-3-phenyl propyl alcohol was obtained through direct reduction from raw materials L-phenylalanine as chiral sources. Also,2-dimethyl amine-5-trifluoro-methyl benzaldehyde was obtained through formylation reactionfrom intermediate product N,N-dimethyl-4-trifluoromethyl aniline which was prepared by methylation reacting from raw material trifluoromethyl aniline. Then, the new chiral amino alcohols (2S)-2-[(5-trifluoromethyl-2-dimethyl amine)phenyl]methylamino-3-phenyl propyl alcohol was obtained from (2S)-2-amino-3-phenyl propyl alcohol and2-dimethyl amine-5-trifluoromethyl benzaldehyde via condensation and reduction reaction. Meantime, another new chiral amino alcohols (2S)-2-[(5-trifluoromethyl-2-dimethylamine)phenyl]methylamino-1,1,3-triphenyl propyl alcohol was received from another chiral amino alcohol1,1,3-triphenyl-2-amino propyl alcohol which was obtained through formatting from L-phenylalanine and5-trifluoromethyl-2-dimethylamine benzaldehyde as the same way to (2S)-2-[(5-trifluoro-methyl-2-dimethyl amine) phenyl]methylamino-3-phenyl propyl alcohol. The products were characterized by IR,’H-NMR and MS spectroscopy.(2).’H-NMR was empolyed to investigate the enantioselective abilities of the synthesized host molecules as CSA to recognize Ibuprofen and other chiral acid compounds which were chosen as guests. After contrast, it was found that (2S)-2-[(5-trifluoromethyl-2-dimethyl-amine) phenyl]methylamino-1,1,3-triphenyl propyl alcohol exhibited best enan-tioselective recognition ability among those guests.(3). The chiral amino acid tested to have good enantioselective recognition ability was used as chiral catalyst in the asymmetry catalytic oxidation reaction of Omeprazole sulfide, aiming to abtain the asymmetry Esomeprazole magnesium. It had good catalyst abilities after observing, the ee value reached98.3%. There were63pictures,9tables and98references in this paper.