Pd-Catalyzed Cascade Reactions of Aziridines: One-step Access to Complex Tetracyclic Amines

Jonathan Knowles*, Hannah Steeds, Maria Schwarz, Francesca Latter, Kevin Booker-Milburn

*Corresponding author for this work

Research output: Contribution to journalLetterpeer-review

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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.
Original languageEnglish
Pages (from-to)4986-4990
Number of pages5
JournalOrganic Letters
Volume23
Issue number13
Early online date16 Jun 2021
DOIs
Publication statusPublished - 2 Jul 2021

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