Chameleonic Reactivity of Imidoyl Sulfoxonium Ylides: Access to Functionalized Pyrroles and Dihydro-pyridines.

We have found a chameleonic reactivity of imidoyl sulfoxonium ylides. On the one hand, imidoyl sulfoxonium ylides react with electron-deficient reagents, such as alkynyl esters, to lead to the formation of 1,2-dihydro-pyridines. The methyl group attached to the sulfur atom acts as a methylene donor. On the other hand, imidoyl sulfoxonium ylides react with pyridinium 1,4-zwitterionic thiolates, which leads to the formation of functionalized pyrroles. Both transformations feature mild reaction conditions and good functional group tolerance.