title: Vinylogous Reactivity of Oxindoles Bearing Nonsymmetric 3-Alkylidene Groups.
abstract: The γ-functionalization of oxindoles bearing nonsymmetric 3-alkylidene groups via vinylogous Michael-type addition to nitroolefins was realized. The suppression of the interconversion between the E and Z isomers of the starting oxindoles allowed a site-specific diastereoselective and enantioselective transformation. Specific experiments allowed us to establish the rate-determining step of the reaction and to advance a robust hypothesis for the exclusive formation of an s-cis enolate as the only reactive intermediate.
authors.affiliation: Department of Industrial Chemistry "Toso Montanari", Alma Mater Studiorum-University of Bologna, Viale del Risorgimento 4, 40136 Bologna, Italy.
authors.forename: Nicola
authors.initials: N
authors.lastname: Di Iorio
authors.affiliation: Department of Industrial Chemistry "Toso Montanari", Alma Mater Studiorum-University of Bologna, Viale del Risorgimento 4, 40136 Bologna, Italy.
authors.forename: Paolo
authors.initials: P
authors.lastname: Righi
authors.affiliation: Department of Industrial Chemistry "Toso Montanari", Alma Mater Studiorum-University of Bologna, Viale del Risorgimento 4, 40136 Bologna, Italy.
authors.forename: Silvia
authors.initials: S
authors.lastname: Ranieri
authors.affiliation: Department of Industrial Chemistry "Toso Montanari", Alma Mater Studiorum-University of Bologna, Viale del Risorgimento 4, 40136 Bologna, Italy.
authors.forename: Andrea
authors.initials: A
authors.lastname: Mazzanti
authors.affiliation: Department of Industrial Chemistry "Toso Montanari", Alma Mater Studiorum-University of Bologna, Viale del Risorgimento 4, 40136 Bologna, Italy.
authors.forename: Riccardo G
authors.initials: RG
authors.lastname: Margutta
authors.affiliation: Department of Industrial Chemistry "Toso Montanari", Alma Mater Studiorum-University of Bologna, Viale del Risorgimento 4, 40136 Bologna, Italy.
authors.forename: Giorgio
authors.initials: G
authors.lastname: Bencivenni