A new synthetic route to polyhydrogenated pyrrolo[3,4-b]pyrroles by the domino reaction of 3-bromopyrrole-2,5-diones with aminocrotonic acid esters

Abstract

A new synthetic approach to polyfunctional hexahydropyrrolo[3,4-b]pyrroles was developed based on cyclization of N-arylbromomaleimides with aminocrotonic acid esters. A highly chemo- and stereoselective reaction is a Hantzsch-type domino process, involving the steps of initial nucleophilic C-addition or substitution and subsequent intramolecular nucleophilic addition without recyclyzation of imide cycle.