Asymmetric Nitro-Aldol Reaction Of Isatins And Nitromethane And Synthesis Of Sulfoxides Catalyzed By Organic Hydrogen Phosphate

1. The synthesis of chiral catalystsAccording to the methods from the literatures, the following catalysts weresynthesized and the ability of these catalysts were studied. The Bifunctional CinchonaAlkaloid derivatives catalysts were obtained from quinine or quinidine through one ortwo steps; A series of symmetrical thiourea catalysts have been synthesized using chiralamino acid as row materials through a multistep; L-proline were used to preparecorresponding thiourea and a series of chiral amino alcohols.2. Investigation on the Asymmetric Nitro-aldol reaction of Isatins withNitromethaneThe enantioselective nitroaldol reactions of isatins with nitroalkanes weresuccessfully realized by organocatalysis. A C’6-OH cinchona alkaloid derivative bearinga C9-OBn group exhibited outstanding catalytic efficiency as an acid–base bifunctionalcatalyst for the nitroaldol reaction of nitromethane to isatins, providing3-hydroxy-3-(nitromethyl)indolin-2-ones in good yields (90–98%) and with good tohigh enantioselectivity (72–95%). The resultant oxindole derivatives are highlyimportant for the synthesis of related natural products and pharmaceutically activecompounds.3. Investigation on the Synthesis of Sulfoxides Catalyzed by Organic HydrogenPhosphate The oxidation of sulfide was carried out by using diphenyl hydrogen phosphate asthe organocatalyst and aqueous hydrogen peroxide as the terminal oxidant. Thecorresponding sulfoxide compounds are obtained in good to excellent yields (81–99%)with excellent diastereoselectivity (92:8to>99:1dr). This method is simplicity, highefficiency, low catalyst loading and good functional group compatibility.