Stereoselective two-carbon ring expansion of allylic amines via electronic control of palladium-promoted equilibria

Charles P. Mikan, Aidan Matthews, Daniel Harris, Charlotte E. McIvor, Paul G. Waddell, Mark T. Sims, Jonathan P. Knowles

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)
18 Downloads (Pure)

Abstract

General methodologies enabling the two-carbon homologation of pyrrolidine and piperidine systems have yet to be developed. Herein we report that palladium-catalysed allylic amine rearrangements enable efficient two-carbon ring expansion of 2-alkenyl pyrrolidine and piperidines to their azepane and azocane counterparts. Conditions are mild, tolerant of a range of functional groups and the process can occur with high enantioretention. The products formed undergo a range of orthogonal transformations, making them ideal scaffolds for the creation of compound libraries.
Original languageEnglish
Article numberd3sc02303f
Pages (from-to)6992-6996
Number of pages5
JournalChemical Science
Volume14
Issue number25
Early online date6 Jun 2023
DOIs
Publication statusPublished - 7 Jul 2023

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