title: Enantioselective cross-coupling of meso-epoxides with aryl halides.
abstract: The first enantioselective cross-electrophile coupling of aryl bromides with meso-epoxides to form trans-β-arylcycloalkanols is presented. The reaction is catalyzed by a combination of (bpy)NiCl2 and a chiral titanocene under reducing conditions. Yields range from 57 to 99% with 78-95% enantiomeric excess. The 30 examples include a variety of functional groups (ether, ester, ketone, nitrile, ketal, trifluoromethyl, sulfonamide, sulfonate ester), both aryl and vinyl halides, and five- to seven-membered rings. The intermediacy of a carbon radical is strongly suggested by the conversion of cyclooctene monoxide to an aryl [3.3.0]bicyclooctanol.
authors.affiliation: Department of Chemistry, University of Rochester , Rochester, New York 14627-0216, United States.
authors.forename: Yang
authors.initials: Y
authors.lastname: Zhao
authors.forename: Daniel J
authors.initials: DJ
authors.lastname: Weix
mesh_terms: D001965:Bromides / Q000737:chemistry; D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D004952:Esters / Q000737:chemistry; D004987:Ethers / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D009532:Nickel / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001965:Bromides; D004852:Epoxy Compounds; D004952:Esters; D004987:Ethers; D007659:Ketones; D009942:Organometallic Compounds; C406884:titanocene; C022838:nickel chloride; D009532:Nickel