Research On The Synthesis Of 3-Substituted-3-hydroxy Oxindole Catalyzed By Chiral Semi-azacrown Ether Ligand

In this thesis, we have committed ourselves to reaearch the asymmetric synthesis of 3-substituted-3-hydroxyoxindole catalyzed by the organometallic catalyst. The addition of isatins to hydrazine can go under mild condition and the scope of substrates is quite wide. Besides that, novel 3,3’-disubsituted oxindoles was prepared through derivatization of products. Thus we offer an efficient method to synthesize the 3,3’-disubsituted oxindoles.3,3’-disubsituted oxindoles can be widely used for total synthesis of pharmaceuticals, so they get a lot of attention because of their potential application value. Therefore we developed the addition of formaldehyde tert–butyl hydrazone to isatins catalyzed by dinuclear zinc catalyst to synthesis chiral 3-substituted-3-hydroxyoxindole. After that we optimized the experimental conditions such as catalyst, solvent, additive and temperature to improve yield and ee. It was found that at the optimal conditions the asymmetric addition can afford the products in good results(up to 98% yield, up to 97% ee). The scope of reaction was explored with a range of isatin derivatives most of which attained satisfactory results(>90% yield, >90% ee). And a possible mechanism was proposed. Eventually, derivatization of products was investigated. Through 3 steps a novel 3,3’-disubsituted oxindole bearing adjacent quaternary-tertiary center was afforded.