Domino Staudinger/aza-Wittig/Mannich Reaction: An Approach to Diversity of Di- and Tetrahydropyrrole Scaffolds

A highly efficient and selective domino reaction producing valuable di‐ and tetrahydropyrrole‐based skeletons from azidoethyl‐substituted CH‐acids and (thio)carbonyl compounds has been developed. By involving the additional functional groups in starting compounds into the domino reaction or postmodification of the primary reaction products, the simple construction of the pharmaceutically relevant three‐ and polycyclic azaheterocyclic scaffolds was demonstrated. Azides’ fairy tail: A new domino sequence was designed based on multifunctional azidoethyl‐substituted CH‐acids. These substrates were shown to be excellent building blocks for the synthesis of a broad variety of highly substituted di‐ and tetrahydropyrroles, including optically active ones, as well as pyrrolidine‐derived tri‐ and polycyclic nitrogen‐containing scaffolds.