Organic Synthesis

Research from the lab of Prof. Syed R. Hussaini

Our group is interested in the development of selective C–C bond forming methods and the use of these methods in the synthesis of bioactive compounds. We are also interested in the application of our methods in domino sequences.

 
Presently, we are investigating efficient methods for the preparation of enaminones. Enaminones have long been used as synthetic intermediates in organic synthesis. They can react with electron rich as well as electron deficient compounds. Therefore, the development of methods that can provide access to a broad range of enaminones is valuable. We have developed a ruthenium catalyzed method that couples diazocarbonyl compounds and thioamides [1]. The reaction is successful with different Grubbs’ catalysts. Presently, efforts are underway to carry out this reaction with the help of more economical catalysts and under photochemical reaction conditions.

The Eschenmoser coupling reaction condenses a thioamide and an alpha-halocarbonyl compound to give enaminones. We have recently developed sonication accelerated version of the Eschenmoser Coupling reaction [2]. Reaction conditions have reduced the time for the completion of reaction from days to hours. Presently, efforts are underway to further reduce the time of reaction into minutes by manipulating the reaction conditions.

References

1. "Ruthenium catalyzed synthesis of enaminones", N. D. Koduri, H. Scott, B. Hileman, J. D. Cox, M. Coffin, L. Glicksberg and S. R. Hussaini, Org. Lett., 2012, 14, 440–443.


2. "Acceleration of the Eschenmoser Coupling Reaction by Sonication: Efficient Synthesis of Enaminones", N. D. Koduri, B. Hileman, J. D. Cox, H. Scott, P. Hoang, A. Robbins, K. Bowers, L. Tsebaot, K. Miao, M. Castaneda, M. Coffin, G. Wei, T. D. W. Claridge, K. P. Roberts and S. R. Hussaini, RSC Advances, 2013, 3, 181–188.