title: Palladium-catalyzed alkoxyamination of alkenes with use of N-fluorobenzenesulfonimide as oxidant.
abstract: A Pd-catalyzed alkoxyamination of protected aminoalkenes promoted by N-fluorobenzenesulfonimide is described. This mild transformation allows the direct formation of ethers from carbon-carbon double bonds. An unusual switch from exo to endo selectivity in polar solvents was discovered, allowing the selective formation of either regioisomer by careful choice of reaction conditions.
authors.affiliation: Department of Chemistry, University of Washington, Box 351700, Seattle, Washington 98195-1700, USA.
authors.forename: Dmitry V
authors.initials: DV
authors.lastname: Liskin
authors.forename: Paul A
authors.initials: PA
authors.lastname: Sibbald
authors.forename: Carolyn F
authors.initials: CF
authors.lastname: Rosewall
authors.forename: Forrest E
authors.initials: FE
authors.lastname: Michael
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000586:Amination; D002384:Catalysis; D003500:Cyclization; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*; D000096926:Benzenesulfonamides
chemical_list: D000475:Alkenes; D004987:Ethers; D010165:Palladium; D013449:Sulfonamides; C523711:N-fluorobenzenesulfonimide; D000096926:Benzenesulfonamides