title: A diastereoselective intermolecular heck reaction of 1,3-dioxepins.
abstract: A highly diastereoselective intermolecular Heck reaction of 1,3-dioxepins is reported. Substitution at both the 2- and 4-positions of the dioxepin directs the Pd coordination and subsequent olefin insertion to provide the trans-disubstituted adduct in good yield and high diastereoselectivity. Chemoselective Heck reaction occurs at the dioxepin alkene in the presence of other olefinic functional groups. A labeling study has been conducted which suggests that the reaction is under kinetic control.
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
authors.forename: Christopher G
authors.initials: CG
authors.lastname: Nasveschuk
authors.forename: Jeffrey D
authors.initials: JD
authors.lastname: Frein
authors.forename: Nathan T
authors.initials: NT
authors.lastname: Jui
authors.forename: Tomislav
authors.initials: T
authors.lastname: Rovis
mesh_terms: D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010082:Oxepins / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D004988:Ethers, Cyclic; D010082:Oxepins