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A multicomponent approach for the stereoselective synthesis of atropisomeric N–N peptide analogues

Lookup NU author(s): Natalie Roper, George Hardy, Dr Jack Wootton, Dr Paul Waddell, Dr Roly ArmstrongORCiD

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This work is licensed under a Creative Commons Attribution 4.0 International License (CC BY 4.0).

Abstract

Peptide analogues featuring both central and N–N axial chirality were efficiently synthesised using a 4-component Ugi reaction. This method demonstrates a broad substrate scope, affording the target compounds with excellent stereoselectivity (up to >95 : 5 d.r.). Thermal atropisomerization studies revealed the identity of the substituents significantly influences the configurational stability and thermodynamic preferences of the atropisomeric products.

Publication metadata

Author(s): Roper NJ, Hardy GM, Wootton JM, Waddell PG, Wilson J, Armstrong RJ

Publication type: Article

Publication status: Published

Journal: Chemical Communications

Year: 2025

Pages: epub ahead of print

Online publication date: 13/10/2025

Acceptance date: 06/10/2025

Date deposited: 13/10/2025

ISSN (print): 1359-7345

ISSN (electronic): 1364-548X

Publisher: Royal Society of Chemistry

URL: https://doi.org/10.1039/D5CC05091J

DOI: 10.1039/D5CC05091J

Data Access Statement: The data underlying this study are available in the published article and in the supplementary information (SI). Supplementary information: detailed experimental procedures and characterization data for new compounds. See DOI: https://doi.org/10.1039/d5cc05091j. CCDC 2476444 and 2476445 contain the supplementary crystallographic data for this paper.

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