Login / Signup

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

Hannah G SteedsJonathan P KnowlesWai L YuJeffery RichardsonKatie G CooperKevin I Booker-Milburn
Published in: Chemistry (Weinheim an der Bergstrasse, Germany) (2020)
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.
Keyphrases
  • dna binding
  • case control
  • reduced graphene oxide
  • transcription factor
  • gold nanoparticles
  • quantum dots