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Lookup NU author(s): Aaron Campbell,
Dr Roly ArmstrongORCiD
This work is licensed under a Creative Commons Attribution 4.0 International License (CC BY 4.0).
Atropisomeric molecules are a privileged class of stereogenic material that have important applications in catalysis, materials science and medicines. To date, the majority of work has been focused upon biaryl and heterobiaryl scaffolds involving restricted rotation between a pair of cyclic fragments, but C–N atropisomeric molecules based upon amines and amides where the nitrogen atom is not part of a ring system are rapidly emerging as an important class of stereogenic molecules. This is the focus of this Short Review article, which begins by discussing the factors which influence the configurational stability of such molecules and provides a historical background to their synthesis. This is followed by a detailed discussion of state-of-the-art catalytic asymmetric strategies that are now available to access C–Nacyclic atropisomers including carboxamides, sulfonamides, sulfinamides, phosphamides and diarylamines. A variety of different synthetic approaches are discussed including kinetic resolution/desymmetrization, amination, C–H functionalization, N-functionalization, and annulation.
Author(s): Campbell ADG, Armstrong RJ
Publication type: Article
Publication status: Published
Online publication date: 21/02/2023
Acceptance date: 20/02/2023
Date deposited: 21/02/2023
ISSN (electronic): 0039-7881
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