Cicloaddizione [3+2] multi-catalitica diastereoselettiva tra vinilciclopropani e N-arilimmine per la sintesi di pirrolidine polifunzionalizzate

In this work, a new diastereoselective [3+2] cycloaddition between N-arilimines and vinylcyclopropanes was developed. Through a synergistic catalysis methodology, this reaction affords polyfunctional pyrrolidines. Initially, it was demonstrated the importance of employing an acid catalyst for the success of the reaction, working synergistically with a palladium (0) catalyst. Subsequently, the reaction conditions were optimized and the scope of the reaction was demonstrated. Moreover, the relative configuration of the two diastereoisomers was determinated by NMR-NOESY analysis. In order to explain this result, a stereochemical model was proposed. Finally, a preliminary enantioselctive version of the reaction was developed using a chiral phosphoric acid as catalyst.