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Synthesis, Structure and Stereodynamics of Atropisomeric N‑Chloroamides

Lookup NU author(s): Aaron Campbell, Natalie Roper, Dr Paul Waddell, Dr Corinne Wills, Dr Casey Dixon, Dr Roly ArmstrongORCiD

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Abstract

Atropisomeric N-chloroamides were efficiently accessed by electrophilic halogenation of ortho-substituted secondary anilides. The stereodynamics of atropisomerism in these novel scaffolds was interrogated by detailed experimental and computational studies, revealing that racemization is correlated with amide isomerization. The stereoelectronic nature of the amide was shown to significantly influence racemization rates, with potentially important implications for other C-N atropisomeric scaffolds.

Publication metadata

Author(s): Campbell ADG, Roper NJ, Waddell PG, Wills C, Dixon CM, Denton RM, Ermanis K, Armstrong RJ

Publication type: Article

Publication status: Published

Journal: Chemical Communications

Year: 2024

Volume: 60

Issue: 28

Pages: 3818-3821

Print publication date: 11/04/2024

Online publication date: 08/03/2024

Acceptance date: 07/03/2024

Date deposited: 08/03/2024

ISSN (electronic): 1364-548X

Publisher: Royal Society of Chemistry

URL: https://doi.org/10.1039/D4CC00268G

DOI: 10.1039/D4CC00268G

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