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Updated: Nov 2, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Pd-Catalyzed Cascade Reactions of Aziridines: One-Step Access to Complex Tetracyclic Amines
Jonathan P Knowles1, Hannah G Steeds2, Maria Schwarz2
1Department of Applied Sciences, Northumbria University, Newcastle upon Tyne NE1 8ST, U.K.
Abstract:
The combination of palladium catalysis and thermal cycloaddition is shown to transform tricyclic aziridines into complex, stereodefined tetracyclic products in a single step. This highly unusual cascade process involves a diverted Tsuji-Trost sequence leading to a surprisingly facile intramolecular Diels-Alder reaction. The starting materials are accessible on multigram scales from the photochemical rearrangement of simple pyrroles. The tetracyclic amine products can be further elaborated through routine transformations, highlighting their potential as scaffolds for medicinal chemistry.
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