Cascade of the acylation/intramolecular oxo-Diels–Alder reaction for the diastereoselective synthesis of thienyl substituted hexahydropyrano[3,4-c]pyrrole-1,6-diones

Abstract

We have developed an efficient approach toward the synthesis of functionalized hexahydropyrano[3,4-c]pyrrole-1,6-diones from readily accessible 3-thienylsubstituted allylamines and maleic anhydride. This transformation begins with the N-acylation of the allylamines with the anhydride, followed by the intramolecular oxo-Diels–Alder reaction (IMODA), which is accompanied by the tautomerization step, and ends with the formation of saturated pyrano[3,4-c]pyrroles.