Nickel-catalyzed asymmetric Ullmann coupling for the synthesis of axially chiral tetra-ortho-substituted biaryl dials.
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.
Chen
Wen-Wen
WW
Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
Zhao
Qian
Q
Xu
Ming-Hua
MH
Lin
Guo-Qiang
GQ
D002384:Catalysis; D009532:Nickel / Q000737:chemistry*; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D011083:Polycyclic Compounds; D009532:Nickel