Carbamate-directed benzylic lithiation for the diastereo- and enantioselective synthesis of diaryl ether atropisomers

Abigail Page, Jonathan Clayden

    Research output: Contribution to journalArticlepeer-review

    Abstract

    Diaryl ethers carrying carbamoyloxymethyl groups may be desymmetrised enantio- and diastereoselectively by the use of the sec-BuLi-(-)-sparteine complex in diethyl ether. Enantioselective deprotonation of one of the two benzylic positions leads to atropisomeric products with ca. 80:20 e.r.; an electrophilic quench typically provides functionalised atropisomeric diastereoisomers in up to 97:3 d.r. © 2011 Page and Clayden; licensee Beilstein-Institut.
    Original languageEnglish
    Pages (from-to)1327-1333
    Number of pages6
    JournalBeilstein Journal of Organic Chemistry
    Volume7
    DOIs
    Publication statusPublished - 23 Sep 2011

    Keywords

    • Configurational stability
    • Diaryl ether
    • Diastereoselective
    • Enantioselective
    • Lateral lithiation
    • Metallation

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