Synthesis of chiral piperazinones using amphoteric aziridine aldehyde dimers and functionalized isocyanides.

We have evaluated a range of functionalized isocyanides in the azitidine aldehyde-driven multicomponent synthesis, of pip erazinones. High diasteroselectivity for each isocyanide was observed. A theoretical evaluation of the reaction course corroborates the experimental data. Moreover, the reactivity of cis- and trans-configured aziridine aldehyde dimers has been compared. This study further probes the dimer-driven mechanism of cyclization and enables an efficient access to a wide range of chiral piperazinones bearing functionalized side chains.