Studies On The Carbon-carbon Coupling Reactions Of α-Oxoketene Dithioacetals In The Conditions Of Catalyst

α-oxo ketene-(S, S)-acetals chemistry has became more and more popular through the development of near one hundred years since theα-benzoyl ketene-(S, S)-acetal was first synthesized by kelber in 1910. Because of it is easy synthesized and with many functional ports,α-oxo ketene dithioacetal is recognized as an important intermediate in organic synthesis. Especially in the near 30 years,α-oxo ketene dithioacetal was playing an important role in the organic chemistry. many excellent articles about this field are published, including several summaries.Besides, the carbon-carbon bond formation is of great importance in the organic chemistry. Particularly, the carbon-carbon bond coupling and forming substituted benzene reaction has been received extensively attention. The special stereoelectronic effect of the alkylthio functionalities which are significant to the carbon-carbon bond formation also play an important role in theα-oxo ketene dithioacetal chemistry.My work is based on the synthesis ofα-oxo ketene (S, S)-acetals, to discuss the carbon-carbon bond formation betweenα-oxo ketene dithioacetal and carbon negative ion in the presence of catalysts. By this method, we can provide a general and simple [5C+1C] route to form multisubstituted phenyl derivatives.First, series ofα-oxo ketene-(S, S) acetals were prepared with high yield based on the reported literatures.Second, in the reaction with salicylaldehyde, m-Hydroxybenzaldehyde and p-Hydroxybenzaldehyde, different kinds of big conjugated system can be readily available under the effect of alkali. Thereby, we can text their biologic activity.In the end, the C=C bond ofα-oxo ketene-(S, S)-acetals can be Deoxidized in the acid condition. Afterwards, under the action of catalyst, nine kinds of polysubstituted aromatic compounds can be easily synthesized via [5C+1C] annulation strategies.