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*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

18 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)296-299
Number of pages4
JournalOrganic Letters
Volume13
Issue number2
Early online date17 Dec 2010
DOIs
Publication statusPublished - 21 Jan 2011

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