title: Geometry-selective synthesis of E or Z N-vinyl ureas (N-carbamoyl enamines).
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.
authors.affiliation: School of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL, UK.
authors.forename: Julien
authors.initials: J
authors.lastname: Lefranc
authors.forename: Daniel J
authors.initials: DJ
authors.lastname: Tetlow
authors.forename: Morgan
authors.initials: M
authors.lastname: Donnard
authors.forename: Alberto
authors.initials: A
authors.lastname: Minassi
authors.forename: Erik
authors.initials: E
authors.lastname: Gálvez
authors.forename: Jonathan
authors.initials: J
authors.lastname: Clayden
mesh_terms: D000577:Amides / Q000737:chemistry; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D007097:Imines / Q000737:chemistry; D017953:Isocyanates / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism; D014508:Urea / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000577:Amides; D000588:Amines; D007097:Imines; D017953:Isocyanates; D009942:Organometallic Compounds; D014753:Vinyl Compounds; D012428:Ruthenium; D014508:Urea