Design And Synthesis Of New Chiral Organic Catalysis

Chrial vicinal diamine compounds with a C₂ axial symmetry were important kinds of chiral catalyst. A verity of new catalyst with high catalytic activity and enantioselectivity was derived from them.Thiourea organic catalyst was a new kind of asymmetric catalyst developing fast recently. It could catalyze many reactions, improve reaction yield, enhance reaction rate and stereoselectivity especially.The structural unique and complex structure of Quinine made it show strong promise for asymmetric syntheses. Chiral quaternary ammonium salt catalyst synthesized by Cinchona alkaloids showed high catalytic activity in asymmetric catalytic reaction.To enhance the hydrogen bonds formation capacity of catalyst, three chiral acyl thiourea catalysts were designed and synthesized. 1 was synthesized from （S,S）- 1,2-diphenyl-1,2-diamine ethane with benzoyl isothiocyanate. 2 was synthesized from （S）-α-phenylethylamine with m-dibenzoyl diisothiocyanate. From （S,S）-1,2-cycloh- exyl diamine tartrate, 3 was synthesized with benzoyl isothiocyanate by five steps.Three compounds was obtained by column chromatography, identified by ¹H-NMR and ¹³H-NMR.We also designed and synthesized three Quninine chiral quaternary ammonium salts. 4 was synthesized from 9-bromo-philippine with Quninine. From o-aminobenz- oic acid, by diazotization, esterification, reduction reaction and bromation, 5 was synthesized with Quninine by five steps. 6 was synthesized by trichloropyrimidine with Quninine.Because of the complex sturcture and strong polarity, the three chiral quaternary ammonium salt catalysts was not purified and structural characterized.