Organocatalytic Asymmetric Chlorination Of 3-Aryloxindoles And Synthesis Of Novel Organocatalysts Based On Dihydroindene Skeleton And Their Initial Applications In Catalytic Asymmetric Reactions

This thesis focused on the cinchona alkaloid catalyzed enantioselective chlorination of 3-aryloxindoles; synthesis of novel biprolinamides and thiourea catalysts based on dihydro indene skeleton and their initial applications in catalytic asymmetric reactions.A series of inexpensive and readily available cinchona alkaloid organocatalysts were synthesized, and applied in the enantioselective chlorination of 3-aryloxindoles and NCS as the chlorination reagent for the first time. The benzoylquinidine 1-11 was found to be the best catalyst, and the corresponding chlorinated products were obtained in excellent yield (81-99% yield) and up to 93% ee. Both the electronic property and steric nature of the substituents on the oxindoles and aromatic rings at C-3 position were examined, including different N-protecting groups. This approach provided an operationally simple protocol to access highly enantiomerically enriched chlorine-containing compounds.Novel biprolinamides and amino-thiourea catalysts derived from (1R,2S)-1-amino-2,3-dihydro-lH-inden-2-ol have been synthesized by optimization of synthetic route and the initial investigation on the asymmetric catalytic reaction have been explored. These two type catalysts have shown some catalytic activity in aldol reaction and the Michael addition between 3-aryloxindole and phenyl vinyl sulfone.