The Synthesis And Catalytic Application Of Amino Acid Derivatives And Design Synthesis And Application Of BINOL Dipeptide Ligands

This article is divided into two parts：The first part：Since the N,N-disubstituted-L-phenylalanine derivatives was confirmed inhibition ofhepatitis C virus NS5B polymerase, compounds with similar structures has received extensiveattention. And the analogues could selectivity over human polymerases.Fourteen N, N-disubstituted-L-phenyl alanine derivatives have been synthesized fromL-phenylalanine with aromatic aldehydes as the raw materials. As substrate thesederivatives been used in Buchwald-Hartwig, with catalyst reacted of complexes ferrocenylimidazoline ligands and palladium, and In the presence of base. Thus expect to get thebiological activity of aromatic ammonia compounds. Study, not getting the expected productsunder the selected conditions. Further catalyst, alkaline conditions, solvent and substratestructure has changed, still not getting the expected products. Follow-up research is stillunderway.The second partCyanhydrin compounds, because of its excellent convertibility, being used for thesynthetic of important organic compounds. As an important organic intermediate, theasymmetries synthetic of cyanhydrin has always been important topic in the organic synthesis.This paper has summarized resorted to the research results of asymmetric catalytic syntheticcyanhydrin, and to silicon cyanide response and hydrocyanation reaction conductedsummarized in recent years. In this part, introduces the ligands and catalyst with differentstructure have good performance in the cyanation reactionï¼›and summarized the products ofthis reaction as important intermediates to the synthesis of natural products and thecompounds with biological activity or drug activity.This thesis, the chiral amino acids and chiral BINOL as the chiral source, designed andsynthesized five BINOL-peptide ligands. And the structure of the synthesized ligands werecharacterized. As ligand and Ti（OiPr）₄after the reaction of benzaldehyde silicon cyanidereaction conditions has been a preliminary study, and from the catalyst, The amount ofcatalyst, the reaction time, reaction temperature, solvent and the ratio of ligand and Ti（OiPr）₄,the six aspects of the reaction yield and ee were studied. Obtained in dichloromethane solvent use of BINOL-L-phenylpropionate-Valeriana two peptide ligands in the L/Ti （OiPr）4=2:1,under the conditions of-20°C for12h, can get the besteffect.Under the selected conditions, the reaction can be carried out smoothly, through theoptimization of the conditions of33%e.e. and almost quantitative conversion rate wasdisplayed. We will continue to silicon cyanide reaction of aromatic aldehydes to expect toimprove the reaction enantioselectivity, and the appropriate substrate expansion.