title: Diastereoselective Synthesis of γ-Substituted 2-Butenolides via (CDC)-Rh-Catalyzed Intermolecular Hydroalkylation of Dienes with Silyloxyfurans.
abstract: Catalytic intermolecular hydroalkylation of dienes with silyloxyfuran nucleophiles is reported. Reactions are catalyzed by 5 mol % of a (CDC)-Rh complex and proceed in up to 87% yield and 6:1 dr (syn/anti) to provide allylic butenolides bearing vicinal stereocenters. Reactions proceed with terminal aryl and alkyl dienes and with modified silyl enol ether nucleophiles including a thiophenone variant. Utility of the products is demonstrated in the synthesis of a polypropionate anti,syn-stereotriad.
authors.affiliation: Department of Chemistry, The University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599-3290, United States.
authors.forename: Matthew J
authors.initials: MJ
authors.lastname: Goldfogel
authors.affiliation: Department of Chemistry, The University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599-3290, United States.
authors.forename: Courtney C
authors.initials: CC
authors.lastname: Roberts
authors.affiliation: Department of Chemistry, The University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599-3290, United States.
authors.forename: Rajith S
authors.initials: RS
authors.lastname: Manan
authors.affiliation: Department of Chemistry, The University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599-3290, United States.
authors.forename: Simon J
authors.identifier: 0000-0001-7537-9420
authors.initials: SJ
authors.lastname: Meek