Carbolithiation of N-alkenyl ureas and N-alkenyl carbamates

Julien Lefranc, Alberto Minassi, Jonathan Clayden

    Research output: Contribution to journalArticlepeer-review


    N-Alkenyl ureas and N-alkenyl carbamates, like other N-acyl enamines, are typically nucleophilic at their β-carbon. However, by incorporating an α-aryl substituent, we show that they will also undergo attack at the β-carbon by organolithium nucleophiles, leading to the products of carbolithiation. The carbolithiation of E and Z N-alkenyl ureas is diastereospecific, and N-tert-butoxy-carbonyl N-alkenyl carbamates give carbolithiation products that may be deprotected in situ to provide a new connective route to hindered amines. © 2013 Lefranc et al.
    Original languageEnglish
    Pages (from-to)628-632
    Number of pages4
    JournalBeilstein Journal of Organic Chemistry
    Publication statusPublished - 28 Mar 2013


    • Carbamate
    • Carbolithiation
    • Carbometallation
    • Organolithium
    • Stereospecificity
    • Styrene
    • Urea


    Dive into the research topics of 'Carbolithiation of N-alkenyl ureas and N-alkenyl carbamates'. Together they form a unique fingerprint.

    Cite this