title: Gold(I)-Assisted α-Allylation of Enals and Enones with Alcohols.
abstract: The intermolecular α-allylation of enals and enones occurs by the condensation of variously substituted allenamides with allylic alcohols. Cooperative catalysis by [Au(ItBu)NTf2] and AgNTf2 enables the synthesis of a range of densely functionalized α-allylated enals, enones, and acyl silanes in good yield under mild reaction conditions. DFT calculations support the role of an α-gold(I) enal/enone as the active nucleophilic species.
authors.affiliation: Department of Chemistry "G. Ciamician", Alma Mater Studiorum-University of Bologna, via Selmi 2, 40126, Bologna (Italy).
authors.forename: Marco Michele
authors.initials: MM
authors.lastname: Mastandrea
authors.affiliation: Department of Chemistry "G. Ciamician", Alma Mater Studiorum-University of Bologna, via Selmi 2, 40126, Bologna (Italy).
authors.forename: Niall
authors.initials: N
authors.lastname: Mellonie
authors.affiliation: Department of Chemistry "G. Ciamician", Alma Mater Studiorum-University of Bologna, via Selmi 2, 40126, Bologna (Italy).
authors.forename: Pietro
authors.initials: P
authors.lastname: Giacinto
authors.affiliation: EaStCHEM School of Chemistry, University of St. Andrews, St. Andrews, KY16 9ST (UK).
authors.forename: Alba
authors.initials: A
authors.lastname: Collado
authors.affiliation: EaStCHEM School of Chemistry, University of St. Andrews, St. Andrews, KY16 9ST (UK).|Chemistry Department, College of Science, King Saud University, Riyadh 11451 (Saudi Arabia).
authors.forename: Steven P
authors.initials: SP
authors.lastname: Nolan
authors.affiliation: Department of Chemistry "G. Ciamician", Alma Mater Studiorum-University of Bologna, via Selmi 2, 40126, Bologna (Italy).|Department of Chemistry, Universidad de los Andes, Carrera 1 N° 18A 10, Bogotá (Colombia).
authors.forename: Gian Pietro
authors.initials: GP
authors.lastname: Miscione
authors.affiliation: Department of Chemistry "G. Ciamician", Alma Mater Studiorum-University of Bologna, via Selmi 2, 40126, Bologna (Italy).
authors.forename: Andrea
authors.initials: A
authors.lastname: Bottoni
authors.affiliation: Department of Chemistry "G. Ciamician", Alma Mater Studiorum-University of Bologna, via Selmi 2, 40126, Bologna (Italy). marco.bandini@unibo.it.
authors.forename: Marco
authors.initials: M
authors.lastname: Bandini
keywords: alcohols; allylation; gold catalysis; reaction mechanisms; unsaturated carbonyl compounds