| The chirality is a kind of basic attribute of the nature.The basic biological phenomenon and law of the nature are all created by the chirality (or be called asymmetry).The asymmetric synthesis plays a very important role in the organic synthesis and bout its study is also unfailing.The design and synthesis of chiral ligands is the eternally topic on the asymmetric catalyze studies.BINOL is the representative dihydroxy chiral ligands,which is used widely in the asymmetric catalyze reactions.In this thesis,we synthesized Betti base[1-(α-aminobenzyl)-2- naphthol], N-methyl- 1-(α-aminobenzyl)-2-naphthol and N,N-dimethyl- 1-(α-aminobenzyl) -2-naphthol from 2-naphthol,benzyl formaldehyde and amine by the Mannich reaction,The yield of the produce was 59.6～84.9%.S-enantiomers of Betti base and its derivatives were obtained as 33～47%,e.e.87～99%.and Renantiomers as 37～53%,e.e.82～97%by using an efficient resolution reagent L-(+)-tartaric acid.The(S)-Betti base was also used for preparing the (S)-1-(α-Piperidylbenzyl)-2-naphthol by reacting with pentane diol.In our knowledge,the synthesis and resolution of N-methyl-1-(α-aminobenzyl) -2-naphthol was reported for the first time.The synthesized of Betti base and its derivatives were used to catalyzed the enantioselective deoxidization reaction of aryl ketone with BH3,the raw material ratio(especially the amount of catalyst)and the reaction temperature were investigated.The results showed that these ligands gave birth to efficient asymmetric inducement to the reaction,which brought the yield 70%yield and e.e.91%,and the reaction mechanism was discussed.At the same time,the synthesized Betti base and its derivatives were also used to catalyzed the enantioselective deoxidization reaction of aryl ketone with LiAlH4.The raw material ratio(especially the amount of catalyst)and the reaction temperature were also investigated.The results showed that these ligands gave birth to efficient asymmetric inducement to the reaction,which brought the yield 90%and e.e.87%,and the reaction mechanism was also discussed.Above the research from the thesis,the chiral Betti base and its derivatives were good asymmetric catalyst. |
