Chiral BINOL-amino Acid Schiff Bases And Its Metallic Complexes As Catalysts For Asymmetric Kabachnik-Fields Reaction

The dissertation focuses on the synthesis of the chiral BINOL synthesized by（1,1’-bi-2-aphthol） as a skeleton of amino acid, in the chiral hexadentate ligand and transitionmetal Mn （III） and Ti （IV） complex; With salicylaldehyde, aniline and diphenyl oxidephosphor is a typical Kabachnik-Fields reaction as an example, study of chiral amino acidssepher, chiral amino acids schiff base and schiff base with InCl₃or Zn（OAc）₂two Lewis acid,transition metal complex reaction of asymmetric catalytic effect respectively, and the salicylicaldehyde, aniline was synthesized by the reaction series of diphenyl and diphenyl oxidephosphorus oxides.The first part is the synthesis of chiral amino acid schiff base and catalyticperformance study. β-naphthol as starting material, through phase transfer catalyzing,methoxylation, acylation, synthetize （S） and （R）-3,3’-dimethyl acyl-2,2’ dihydroxy1,1’-BINOL, then under the frame of the compounds, and the chiral amino acid reaction, for thefirst time with one-pot method of five kinds of chiral amino acids schiff base weresynthesized. Five schiff base was studied with InCl₃or Zn（OAc）₂response to cases ofasymmetric catalytic effect, but the ee value measured in HPLC is not high, the highest ataround9%.In the second part Mn （III） complex was synthesized by one-pot method and used forcatalyzing asymmetric Kabachnik-Fields reaction. We found that Mn （III） with L-Tryptophanschiff base complex asymmetric catalytic effect is good, the ee value is as high as90.9%, andthe low temperature condition the ee value inreases to99%, others ee value does not exceed10%; Ti （IV） and the formation of complex compound amino acids has been reportedliterature, we first explore the asymmetric Kabachnik-Fields reaction of catalytic performance.Measured results by HPLC with L-Tryptophan schiff base complex ee value was80.4%, andthe low temperature condition the ee value inreases to90%, other complex catalytic ee valuesare not more than50%.The third part is chiral BINOL amino acid Schiff base of Mn （III） complex as catalyst,catalytic reaction in a series of asymmetric Kabachnik-Fields reaction, HPLC determinationof the ee value, up to53.76%. Compounds （（2-hydroxy phenyl）（benzyl amino） methyl）diphenyl phosphine oxide single crystal diffraction. On the synthesis of compounds¹HNMR,¹³CNMR and³¹PNMR, compounds of materials, Schiff base and complex, also carried onthe NMR and IR structure identification.