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Rapid Access to Azabicyclo[3.3.1]nonanes by a Tandem Diverted Tsuji–Trost Process
Author(s) -
Steeds Hannah G.,
Knowles Jonathan P.,
Yu Wai L.,
Richardson Jeffery,
Cooper Katie G.,
BookerMilburn Kevin I.
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202003762
Subject(s) - tandem , chemistry , combinatorial chemistry , ring (chemistry) , nonane , catalysis , hydride , palladium , scope (computer science) , substrate (aquarium) , stereochemistry , organic chemistry , metal , computer science , materials science , oceanography , composite material , programming language , geology
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.