Rapid Access to Azabicyclo[3.3.1]nonanes via a tandem diverted Tsuji-Trost process

Steeds, Hannah, Knowles, Jonathan, Yu, Wai, Richardson, Jeffery, Cooper, Katie and Booker-Milburn, Kevin (2020) Rapid Access to Azabicyclo[3.3.1]nonanes via a tandem diverted Tsuji-Trost process. Chemistry: A European Journal. ISSN 0947-6539 (In Press)

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Abstract

A three-step synthesis of the 2-azabicyclo[3.3.1]nonane ring system from simple pyrroles, employing a combined photochemical/palladium-catalyzed 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 via acid-assisted C-N bond ß-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.

Item Type: Article
Subjects: B900 Others in Subjects allied to Medicine
F100 Chemistry
Department: Faculties > Health and Life Sciences > Applied Sciences
Depositing User: John Coen
Date Deposited: 24 Aug 2020 10:09
Last Modified: 24 Aug 2020 10:15
URI: http://nrl.northumbria.ac.uk/id/eprint/44170

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