title: Base catalyzed synthesis of bicyclo[3.2.1]octane scaffolds.
abstract: The base-catalyzed reaction of achiral 1,3-cyclopentanediones tethered to activated olefins afforded in high yields bicyclo[3.2.1]octane-6,8-dione or bicyclo[3.2.1]octane-6-carboxylate derivatives bearing respectively three or five stereogenic centers. The course of the reaction is closely related to the reaction time and to the base involved in the reaction.
authors.affiliation: Université de Strasbourg-Institut de Chimie UMR UdS/CNRS 7177, 1 rue Blaise Pascal, 67008 Strasbourg, France. m.miesch@unistra.fr.
authors.forename: Régis
authors.initials: R
authors.lastname: Boehringer
authors.forename: Philippe
authors.initials: P
authors.lastname: Geoffroy
authors.forename: Michel
authors.initials: M
authors.lastname: Miesch
mesh_terms: D000468:Alkalies / Q000737:chemistry; D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002254:Carbonates / Q000737:chemistry; D002264:Carboxylic Acids / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D003517:Cyclopentanes / Q000138:chemical synthesis / Q000737:chemistry; D009795:Octanes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000468:Alkalies; D000475:Alkenes; D001643:Bridged Bicyclo Compounds; D002254:Carbonates; D002264:Carboxylic Acids; D003517:Cyclopentanes; D009795:Octanes; C026728:octane