PyBidine-NiCl2-Catalyzed Asymmetric Addition of Alcohols and Peroxides to Isatin-Derived Ketimines.
An (S,S)-diphenyldiamine-derived bis(imidazolidine)pyridine (PyBidine)-NiCl2 complex catalyzed the asymmetric addition of methanol and peroxides to isatin-derived N-Boc-imines to form chiral quaternary N,O-acetals at the C3 position of the resulting oxiindoles in up to 99% yield with 94% ee.
Department of Chemistry, Graduate School of Science, Chiba University, 1-33 Yayoi, Inage, Chiba 263-8522, Japan.
Takayoshi
T
Arai
Department of Chemistry, Graduate School of Science, Chiba University, 1-33 Yayoi, Inage, Chiba 263-8522, Japan.
Kento
K
Tsuchiya
Department of Chemistry, Graduate School of Science, Chiba University, 1-33 Yayoi, Inage, Chiba 263-8522, Japan.
Eri
E
Matsumura
D000080:Acetals / Q000138:chemical synthesis* / Q000737:chemistry; D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D003959:Diamines / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D007510:Isatin / Q000737:chemistry*; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D009570:Nitriles / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D010545:Peroxides / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*
D000080:Acetals; D000438:Alcohols; D003959:Diamines; D007097:Imines; D009570:Nitriles; D009942:Organometallic Compounds; D010545:Peroxides; D011725:Pyridines; C542835:ketimine; C000601928:pybidine-NiCl2; C022838:nickel chloride; D009532:Nickel; D007510:Isatin