title: Diastereoselective oxidative carbon-carbon bond formation via silyl bis-enol ethers.
abstract: Diisopropylsilyl bis-enol ethers are shown to be powerful intermediates for the diastereoselective dimerization and cross-coupling of cyclic ketones. The trends observed for the oxidative coupling of a range of different dialkylsilyl bis-enol ethers derived from cyclohexanone are rationalized by invoking a stereochemical model based on a Thorpe-Ingold effect.
authors.affiliation: Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, USA.
authors.forename: Christopher T
authors.initials: CT
authors.lastname: Avetta
authors.forename: Leah C
authors.initials: LC
authors.lastname: Konkol
authors.forename: Carla N
authors.initials: CN
authors.lastname: Taylor
authors.forename: Karen C
authors.initials: KC
authors.lastname: Dugan
authors.forename: Charlotte L
authors.initials: CL
authors.lastname: Stern
authors.forename: Regan J
authors.initials: RJ
authors.lastname: Thomson
mesh_terms: D002244:Carbon / Q000737:chemistry; D003500:Cyclization; D003512:Cyclohexanones / Q000737:chemistry*; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D003512:Cyclohexanones; D004987:Ethers; D007659:Ketones; C036468:cyclohexanone; D002244:Carbon