| In this thesis, Syntheses, chiral resolution of 1, 2-diphenyl -2-amino alcohol have been studied, The syntheses of a series of 1, 2-diphenyl 2-amino alcohol derivatives have also been studied.1. The synthetic method of 1,2-diphenyl 2-amino alcohol have been studiedThe catalytic hydrogenation of benzoin oxime to 1, 2-diphenyl-2-amino alcohol with Raney Ni or Pd-C as catalyst was studied. The erythro- and threo- diastereo mixture is formed simultaneously when Raney Ni was used as catalyst whereas only ethreo-racemic products were obtained in the condition of Pd-C. The temperature, solvents, H2 pressure and purity of starting material were found to be major. A hypothesis mechanism of the hydrogenation of benzoin oxime catalyzed by the two types of catalysts is suggested.2. The resolution of erythro-l,2-diphenyI-2-amino alcohol by using 3-ketofuranose xylose as chiral source was studied and the optical pure (1R,2S)-1, 2-diphenyl-2-amino alcohol was easily obtained1). 3-Ketofuranose xylose, which was prepared easily by us, was used as the chiral source, in the resolution of 1,2-diphenyl-2-amino alcohol. The two diastereo isomers obtained in the resolution processes were characterized by IR, !H NMR,13C HMR and polarimeter and their absolute structures were also confirmed by the crystal struture determination. It was shown from the sesults that only the (1R,2S) -l,2-diphenyl-2-amino alcohol condenses with the 3-Ketofuranose xylose to form a xylose derivative. But the (1S,2R) l,2-diphenyl-2-amino alcohol underwant a enzyme mimic process to accelerate the hydrolysis of the extra bond in the 3-Ketofuranose xylose, and then found a supramolecular structure with PhCOOH.2). The optical pure (IR, 2S)-l,2-diphenyl-2-amino alcohol was therefore prepared by hydrolyzing the complex 14 with aquose base which the optical purity is very high have been prepared. Thus the aim to splitting 1, 2-diphenyl-2-amino alcohols have been gained.3. The preparation of polydentate ligands (I-V) with 1, 2-diphenyl-2-amino alcohol as chiral centers(IR, 2S) 1, 2-diphenyl-2-amino alcohol as the chiral source prepared by ourselves have been used to prepare a series of amino alcohol ligands in the reactions with several compounds I-V. Nevertheless the products were all unstable and results were verycomplicated. The reaction mechanism has been studied and discovered the transforming rules and also characterized by MS, IR, 1H NMR spectra. |
