Rapid Access to Azabicyclo[3.3.1]nonanes by a Tandem Diverted Tsuji–Trost Process

Hannah Steeds, Jonathan Knowles, Wai Yu, Jeffery Richardson, Katie Cooper, Kevin Booker-Milburn

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)
12 Downloads (Pure)

Abstract

A three-step synthesis of the 2-azabicyclo[3.3.1]nonane ring system from simple pyrroles, employing a combined photochemical/palladium-catalysed approach is reported. Substrate scope is broad, allowing the incorporation of a wide range of functionality relevant to medicinal chemistry. Mechanistic studies demonstrate that the process occurs by acid-assisted C−N bond cleavage followed by β-hydride elimination to form a reactive diene, demonstrating that efficient control of what might be considered off-cycle reactions can result in productive tandem catalytic processes. This represents a short and versatile route to the biologically important morphan scaffold.

Original languageEnglish
Pages (from-to)14330-14334
Number of pages5
JournalChemistry - A European Journal
Volume26
Issue number63
Early online date6 Oct 2020
DOIs
Publication statusPublished - 11 Nov 2020

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