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

被引：95
作者：
Arai, Takayoshi [1 ]
Matsumura, Eri [1 ]
Masu, Hyuma [2 ]
机构：
[1] Chiba Univ, Grad Sch Sci, Dept Chem, Inage Ku, Chiba 2638522, Japan
[2] Chiba Univ, Ctr Analyt Instrumentat, Inage Ku, Chiba 2638522, Japan
来源：
ORGANIC LETTERS | 2014年 / 16卷 / 10期
关键词：
HIGHLY ENANTIOSELECTIVE ADDITION; ORGANOCATALYTIC ALPHA-AMINATION; PICTET-SPENGLER REACTIONS; AZA-HENRY REACTION; ISOTHIOCYANATO OXINDOLES; EFFICIENT; SPIROOXINDOLES; CONSTRUCTION; COMPLEXES; BEARING;
D O I：
10.1021/ol501085y
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
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页码：2768 / 2771
页数：4
相关论文
共 55 条
  • [1] Arai T., SYNLETT UNPUB
  • [2] The Role of Ni-Carboxylate During Catalytic Asymmetric Iodolactonization Using PyBidine-Ni(OAc)2
    Arai, Takayoshi
    Kajikawa, Satoshi
    Matsumura, Eri
    [J]. SYNLETT, 2013, 24 (16) : 2045 - 2048
  • [3] syn-Selective Asymmetric Mannich Reaction of Sulfonyl Imines with Iminoesters Catalyzed by the N,N,N-Tridentate Bis(imidazolidine)pyridine (PyBidine)-Cu(OTf)2 Complex
    Arai, Takayoshi
    Mishiro, Asami
    Matsumura, Eri
    Awata, Atsuko
    Shirasugi, Mayu
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (36) : 11219 - 11222
  • [4] Chiral Bis(Imidazolidine) Pyridine-Cu Complex-Catalyzed Enantioselective [3+2]-Cycloaddition of Azomethine Imines with Propiolates
    Arai, Takayoshi
    Ogino, Yuta
    [J]. MOLECULES, 2012, 17 (05): : 6170 - 6178
  • [5] Chiral Bis(imidazolidine)pyridine-Cu(OTf)2: Catalytic Asymmetric Endo-Selective [3+2] Cycloaddition of Imino Esters with Nitroalkenes
    Arai, Takayoshi
    Mishiro, Asami
    Yokoyama, Naota
    Suzuki, Kuniko
    Sato, Hiroyasu
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (15) : 5338 - +
  • [6] Enantioselective Pictet-Spengler reactions of isatins for the synthesis of spiroindolones
    Badillo, Joseph J.
    Silva-Garcia, Abel
    Shupe, Benjamin H.
    Fettinger, James C.
    Franz, Annaliese K.
    [J]. TETRAHEDRON LETTERS, 2011, 52 (43) : 5550 - 5553
  • [7] Vasotocin and vasopressin stimulation of the chloride secretion in the human bronchial epithelial cell line, 16HBE14o-
    Bernard, K
    Bogliolo, S
    Ehrenfeld, J
    [J]. BRITISH JOURNAL OF PHARMACOLOGY, 2005, 144 (08) : 1037 - 1050
  • [8] Svnthesis of a new chiral N,N,N-tridentate pyridinebisimidazoline ligand library and its application in Ru-catalyzed asymmetric epoxidation
    Bhor, S
    Anilkumar, G
    Tse, MK
    Klawonn, M
    Dobler, C
    Bitterlich, B
    Grotevendt, A
    Beller, M
    [J]. ORGANIC LETTERS, 2005, 7 (16) : 3393 - 3396
  • [9] Bindra J.S., 1973, The Alkaloids, V14, P84
  • [10] Highly Enantioselective Organocatalytic α-Amination Reactions of Aryl Oxindoles: Developing Designer Multifunctional Alkaloid Catalysts
    Bui, Tommy
    Hernandez-Torres, Gloria
    Milite, Ciro
    Barbas, Carlos F., III
    [J]. ORGANIC LETTERS, 2010, 12 (24) : 5696 - 5699
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