Studies On The Syntheses, Catalytic Activity And Stereoselectivity Of Chiral Amino Alcohols

In this thesis, the syntheses and chiral resolution of thero-1, 2-diphenyl-2-amino alcohol were studied. Some proline based chiral amino alcohols synthesized from commercial available trans-4-hydronxy-L-proline as well as L-proline and their catalytic activities in enantioselective epoxidation of α,β-unsaturated ketones were also studied. 1. Syntheses and chiral resolution of thero-1,2-diphenyl-2-amino alcoholErythro-1, 2-diphenyl-2-amino alcohol was synthesized from benzaldehyde by several steps. The thero-1, 2-diphenyl-2-amino alcohol was obtained successfully by configuration transferation of the corresponding erythro-1, 2-diphenyl-2-aminoalcohol.By using xylofuranose derivative as resolving agent, the racemic threo-1,2 -diphenyl-2-amino alcohol was resoluted easily to its R,R- and S.S-isomers in high yields. An oxazolidinyl spiral compound 2-8 was formed rapidly when stirring the racemic amino alcohol with xylofuranose derivative in a proper solvent and its absolute structure was confirmed to be R, R-configuration by X-ray crystallographic analysis. The structures of conducts were characterized by IR, ~1H NMR, MS and optical rotation spectra. The reaction mechanism has been studied.