Research On The Synthesis Of Fur An And Pyrrolidine Derivatives With Biological Activity

The thesis aims at the synthesis of chiral N,P-ligands,2,3-bisubsituted-5-vinyl-4,5-dihydro-furan derivatives and 2-methylenepyrrole derivatives.1. Series of chiral N,P-ligands with amide or imine groups were synthesized. Firstly, the primary-amine compound were derived from the cinchona alkaloid.Then Through the reaction with 2-(diphenylphosphino oxide) benzoic acid and primary- amine, the simplest chiral N,P-ligands with amide were achieved by the dehydration. At the same time, different chiral N,P-ligands with imine were synthesized with primary-amine compound、amino acid and 2-(diphenylphosphino) benzaldehyde.2. Under the cooperative catalyzation of matalic catalyst and ligands,2,3-bisubsituted-5-vinyl-4,5-dihydrofuran derivatives were synthesized through the intermolecular C-allylation reaction and the intramolecular O-allylation reaction of allyl dicarbonate and β-keton ester. Through optimizing the experiment parameters, 2 mol% Pd(PPh3)4 and 2 mol%1,2-bis(diphenylphosphino)ethane were selected as the highly efficient catalyst system, then series of 2,3-bisubsituted-5-vinyl-4,5- dihydrofuran derivatives were synthesized under the same conditions. The results showed the reaction has high reactivities and yields with electron-withdrawing group. Subsequently, the chiral 2,3-bisubsituted-5-vinyl-4,5-dihydrofuran derivatives were also synthesized by synergistic effect with the present of chiral N,P-ligands and metal. Although the desired product with low enantiomer were presented, it still provided experimental experience and theoretical guidance for further researches.3. Under the cooperative catalyzation of chiral N,P-ligands,metal and base, 2- methylenepyrrolidine derivatives were synthesized with the terminal alkynyl dicarbonate and protected imine as substrates by the cascade cylization of Mannich and hydroamination of alkyne. By the optimization of experimental conditions: metal catalysts,chiral ligands and solvents, the product was successfully obtained with a yield of 83%and enantiomeric excess of 65%.