Isocyanide-based MCRs: Diastereoselective cascade synthesis of perfluoroalkylated pyrano[3,4-c]pyrrole derivatives

Abstract

The highly diastereoselective synthesis of perfluoroalkyl-containing pyrano[3,4-c]pyrroles has been accomplished via a cascade process involving Michael addition, Passerini-type reaction, Mumm rearrangement and an oxo-Diels–Alder reaction. This domino transformation of isocyanides, methyl perfluoroalk-2-ynoates and 3-aroyl (or heteroyl) acrylic acids proceeded smoothly at room temperature and led to the formation of the highly diastereoselective target compounds with high functional-group compatibility in good to excellent yields.