Alchilazione enantioselettiva di ossindoli sostituiti mediata da organocatalizzatori

This thesis summarizes an internship project carried out in part at the University of Zaragoza (Spain) and in part at the University of Bologna. The project involved the development of a new enantioselective catalytic methodology based on an alkylation reaction in order to obtain an oxindole derivative bearing a quaternary chiral center at C3. Such kind of oxindole derivatives have great relevance in farmaceutical chemistry. We started from the synthesis of a new oxindole substrate, successfully adapting methods reported for similar compounds. A screening of benzohydrol alkylating agents was then carried out, which led to the identification of Michler's hydrol as a reactive capable of leading to the alkylation product bearing a quaternary chiral center. A screening of reaction conditions and organic catalysts was then carried out in order to optimize yield and enantiomeric excess. These tests, which led to good yield values and modest enantioselections, made it possible to identify two main classes of promising catalysts and reaction conditions, on which the continuation of the project can focus.