Enantioselective synthesis of an atropisomeric diaryl ether

Jonathan Clayden, Christopher P. Worrall, Wesley J. Moran, Madeleine Helliwell

    Research output: Contribution to journalArticlepeer-review

    Abstract

    (Chemical Equation Presented) Twisted ethers: Introduction of a bulky alkylsulfinyl substituent ortho to the C-O axis of a diaryl ether imposes a powerful conformational preference (see scheme). The preference persists upon oxidation of the sulfoxide to a sulfone, leading to dynamic thermodynamic resolution of the atropisomeric ether. This is the first enantioselective synthesis of an atropisomeric diaryl ether not forming part of a macrocyclic ring. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
    Original languageEnglish
    Pages (from-to)3234-3237
    Number of pages3
    JournalAngewandte Chemie - International Edition
    Volume47
    Issue number17
    DOIs
    Publication statusPublished - 14 Apr 2008

    Keywords

    • Atropisomerism
    • Conformation analysis
    • Diaryl ethers
    • Sulfur

    Fingerprint

    Dive into the research topics of 'Enantioselective synthesis of an atropisomeric diaryl ether'. Together they form a unique fingerprint.

    Cite this