title: Palladium-catalyzed [1,3]-O-to-C rearrangement of pyrans toward functionalized cyclohexanones.
abstract: Functionalized cyclohexanones are prepared from cyclic enol ethers via a Pd-catalyzed [1,3]-O-to-C rearrangement reaction. α-Arylketones are generated with excellent diastereocontrol when basic phosphine ligands are used. In contrast, a Lewis acid is required to promote the rearrangement of the alkyl-substituted enol ether systems.
authors.affiliation: Department of Chemistry, University of Sheffield, Brook Hill, Sheffield, S3 7HF, United Kingdom.
authors.forename: Julien C R
authors.initials: JC
authors.lastname: Brioche
authors.forename: Thomas A
authors.initials: TA
authors.lastname: Barker
authors.forename: David J
authors.initials: DJ
authors.lastname: Whatrup
authors.forename: Michael D
authors.initials: MD
authors.lastname: Barker
authors.forename: Joseph P A
authors.initials: JP
authors.lastname: Harrity
mesh_terms: D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D003512:Cyclohexanones / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D011714:Pyrans / Q000737:chemistry*
chemical_list: D003512:Cyclohexanones; D008024:Ligands; D011714:Pyrans; D010165:Palladium; D002244:Carbon; D010100:Oxygen