Geometry-selective synthesis of e or Z N -vinyl ureas (N -carbamoyl enamines)

Julien Lefranc, Daniel J. Tetlow, Morgan Donnard, Alberto Minassi, Erik Gálvez, Jonathan Clayden

    Research output: Contribution to journalArticlepeer-review


    N-Vinyl ureas are emerging as a valuable class of compounds with both nucleophilic and electrophilic reactivity. They may be made by capturing the enamine tautomer of an imine with an isocyanate, a reaction which in general leads to the E isomer of the vinyl urea. Deprotonation of such a vinyl urea, or of an allyl urea, generates a dipole stabilized Z-allyl anion which may be protonated to return the Z-vinyl urea. Isomerization of an allyl urea with a Ru complex provides an alternative route to E-vinyl ureas. © 2010 American Chemical Society.
    Original languageEnglish
    Pages (from-to)296-299
    Number of pages3
    JournalOrganic Letters
    Issue number2
    Publication statusPublished - 21 Jan 2011


    Dive into the research topics of 'Geometry-selective synthesis of e or Z N -vinyl ureas (N -carbamoyl enamines)'. Together they form a unique fingerprint.

    Cite this