A new Mumm-type rearrangement with dithiocarbamates via isocyanide-based multicomponent reaction under ultrasound irradiation: synthesis of polysubstituted pyrrolidine compounds

Abstract

A novel and efficient multicomponent reaction for the synthesis of polysubstituted pyrrolidine derivatives is described under catalyst-free conditions using ultrasonic irradiation. The reactions were performed via a one-pot four-component condensation of secondary amines, carbon disulfide, isocyanides, and gem-dicyano olefins at room temperature to afford polysubstituted pyrrolidines diastereoselectively in 56–96% yields. This is the first report of a Mumm-type rearrangement with dithiocarbamates followed by intramolecular cyclization, which leads to the preparation of the key structure of pyrrolidine.