title: Nickel-catalyzed asymmetric Ullmann coupling for the synthesis of axially chiral tetra-ortho-substituted biaryl dials.
abstract: The first example of nickel-catalyzed asymmetric Ullmann coupling of bis-ortho-substituted arylhalides is described. With the chiral BINOL-based monodentate phosphoramidite ligand, the reaction allows atropoenantioselective synthesis of a series of axially chiral tetra-ortho-substituted biaryl dials. By taking advantage on this asymmetric Ullman coupling as a key stereogenic axis-forming reaction, the formal synthesis of (+)-isoschizandrin was accomplished.
authors.affiliation: Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
authors.forename: Wen-Wen
authors.initials: WW
authors.lastname: Chen
authors.forename: Qian
authors.initials: Q
authors.lastname: Zhao
authors.forename: Ming-Hua
authors.initials: MH
authors.lastname: Xu
authors.forename: Guo-Qiang
authors.initials: GQ
authors.lastname: Lin
mesh_terms: D002384:Catalysis; D009532:Nickel / Q000737:chemistry*; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D011083:Polycyclic Compounds; D009532:Nickel