title: Propargyl alcohols as β-oxocarbenoid precursors for the ruthenium-catalyzed cyclopropanation of unactivated olefins by redox isomerization.
abstract: An atom-economical method for the direct synthesis of [3.1.0]- and [4.1.0]-bicyclic frameworks via Ru-catalyzed redox bicycloisomerization of enynols is reported. The presented results highlight the unique reactivity profile of propargyl alcohols, which function as β-oxocarbene precursors, in the presence of a ruthenium(II) complex. Furthermore, a rare case of a formal vinylic C-H insertion reaction is described.
authors.affiliation: Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. bmtrost@stanford.edu
authors.forename: Barry M
authors.initials: BM
authors.lastname: Trost
authors.forename: Alexander
authors.initials: A
authors.lastname: Breder
authors.forename: B Michael
authors.initials: BM
authors.lastname: O'Keefe
authors.forename: Meera
authors.initials: M
authors.lastname: Rao
authors.forename: Adam W
authors.initials: AW
authors.lastname: Franz
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D020005:Propanols / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000480:Alkynes; D020005:Propanols; C030011:carbene; D012428:Ruthenium; C028255:propargyl alcohol; D008697:Methane