Organocatalyzed Asymmetric Addition of 3-Aminoxindole with Azodicarboxylates
Chiral 3,3-disubstituted oxyindole structural units are widely found in biologically active natural products and pharmaceutically active compounds,especially in optically active 3-aminoindole oxides.In addition,the chiral 3,3-disubstituted oxyindole structural unit has attracted much attention as an effective antimalarial drug(NITD609),a highly effective anxiety and depression inhibitor(SSR149415),and an HIV protease inhibitor.Therefore,it is of great significance to develop new methods for the synthesis of chiral 3-aminoindole.In order to realize the asymmetric synthesis of N,N'-condensed isatin derivatives,which are sensitive products of the reaction,cinchona base-derived squaramides were used as catalysts,and 3-aminooxidized indole Schiff base and azodicarboxylic acid ester were used as catalysts.Template substrate,the corresponding product was finally obtained with a yield of 70%～85%and an enantioselectivity of 45%～88%.The results show that the experimental conditions of this reaction are mild and the atom economy is high.
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