title: Copper-mediated construction of spirocyclic bis-oxindoles via a double C-H, Ar-H coupling process.
abstract: A double C-H, Ar-H coupling process for the conversion of bis-anilides into spirocyclic bis-oxindoles, enabling the concomitant formation of two all-carbon quaternary centers at oxindole 3-positions in a diastereoselective manner, is described. The optimum cyclization conditions utilize stoichiometric Cu(OAc)2·H2O/KOtBu in DMF at 110 °C and have been applied to prepare a range of structurally diverse bis-spirooxindoles in fair to good yields (28-77%); the method has also been extended to prepare bis-oxindoles linked by a functionalized acyclic carbon chain.
authors.affiliation: Department of Chemistry, University of York , Heslington, York YO10 5DD, U.K.
authors.forename: Pauline
authors.initials: P
authors.lastname: Drouhin
authors.forename: Timothy E
authors.initials: TE
authors.lastname: Hurst
authors.forename: Adrian C
authors.initials: AC
authors.lastname: Whitwood
authors.forename: Richard J K
authors.initials: RJ
authors.lastname: Taylor