Synthesis of Nitrosufones Utilizing Enantioselective Catalyst
Presentation Type
Poster
Faculty Advisor
Magnus Bebbington
Access Type
Event
Start Date
26-4-2024 2:15 PM
End Date
26-4-2024 3:15 PM
Description
The synthesis of sulfones continues to be important in the production of pharmaceuticals. We studied the reaction between the sulfur nucleophile, Sodium-p-toluenesulfinate, and ß- nitrostyrene in attempts to produce useful nitrosulfone building blocks. Previous experiments led to the discovery of the necessary reagents for the desired nitrosulfone product to form as a racemic mixture of enantiomers in yields near 90%. Now, a potentially enantioselective phase transfer catalyst, (-) – N-benzylcinchonidinium chloride, is being utilized in an attempt to produce one enantiomer selectively. Hopeful results have been obtained in 79% yield using said phase transfer catalyst. Reduction of the nitrosulfone to the corresponding amine will allow confirmation of enantioselectivity via chiral HPLC analysis. Current focus is on ensuring the reduction process is feasible in the racemic mixture, and will then be continued for the enatio-enriched product.
Synthesis of Nitrosufones Utilizing Enantioselective Catalyst
The synthesis of sulfones continues to be important in the production of pharmaceuticals. We studied the reaction between the sulfur nucleophile, Sodium-p-toluenesulfinate, and ß- nitrostyrene in attempts to produce useful nitrosulfone building blocks. Previous experiments led to the discovery of the necessary reagents for the desired nitrosulfone product to form as a racemic mixture of enantiomers in yields near 90%. Now, a potentially enantioselective phase transfer catalyst, (-) – N-benzylcinchonidinium chloride, is being utilized in an attempt to produce one enantiomer selectively. Hopeful results have been obtained in 79% yield using said phase transfer catalyst. Reduction of the nitrosulfone to the corresponding amine will allow confirmation of enantioselectivity via chiral HPLC analysis. Current focus is on ensuring the reduction process is feasible in the racemic mixture, and will then be continued for the enatio-enriched product.