Bis(imidazolidine)pyridine-NiCl2 Catalyst for nitro-Mannich reaction of isatin-derived N-Boc ketimines: asymmetric synthesis of chiral 3-substituted 3-amino-2-oxindoles.
An (S,S)-diphenyldiamine-derived bis(imidazolidine)pyridine (PyBidine)-NiCl2 complex catalyzed the nitro-Mannich reaction of isatin-derived N-Boc ketimines to construct a chiral quaternary aminocarbon center at the C3 position of oxindoles in yields of up to 99% with 95% ee.
Department of Chemistry, Graduate School of Science, Chiba University , 1-33 Yayoi, Inage, Chiba 263-8522, Japan.
Takayoshi
T
Arai
Eri
E
Matsumura
Hyuma
H
Masu
D002384:Catalysis; D048289:Imidazolidines / Q000138:chemical synthesis / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007510:Isatin / Q000737:chemistry*; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D009570:Nitriles / Q000737:chemistry*; D000078183:Oxindoles; D011725:Pyridines / Q000737:chemistry
C551521:3-amino-2-oxindole; D048289:Imidazolidines; D007097:Imines; D007211:Indoles; D009570:Nitriles; D000078183:Oxindoles; D011725:Pyridines; C542835:ketimine; C022838:nickel chloride; D009532:Nickel; D007510:Isatin