title: [CpRu]-catalyzed carbene insertions into epoxides: 1,4-dioxene synthesis through S(N)1-like chemistry with retention of configuration.
abstract: Rather than lead to the usual deoxygenation pathway, metal carbenes derived from α-diazo-β-ketoesters undergo three-atom insertions into epoxides using a combination of 1,10-phenanthroline and [CpRu(CH3CN)3][BAr(F)] as the catalyst. Original 1,4-dioxene motifs are obtained as single regio- and stereoisomers. A perfect syn stereochemistry (retention, e.r. up to 97:3) is observed for the ring opening, which behaves as an S(N)1-like transformation.
authors.affiliation: Department of Organic Chemistry, University of Geneva, Quai Ernest Ansermet 30, 1211 Geneva 4 (Switzerland) http://www.unige.ch/sciences/chiorg/lacour/
authors.forename: Thierry
authors.initials: T
authors.lastname: Achard
authors.forename: Cecilia
authors.initials: C
authors.lastname: Tortoreto
authors.forename: Amalia I
authors.initials: AI
authors.lastname: Poblador-Bahamonde
authors.forename: Laure
authors.initials: L
authors.lastname: Guénée
authors.forename: Thomas
authors.initials: T
authors.lastname: Bürgi
authors.forename: Jérôme
authors.initials: J
authors.lastname: Lacour
keywords: carbenes; diazo compounds; ruthenium; stereoselectivity; ylides