Asymmetric organocatalytic N-nitroso-aldol reaction of oxindoles

被引：54
|
作者：
Zhang, Tao [1 ]
Cheng, Liang [1 ]
Liu, Li [1 ]
Wang, Dong [1 ]
Chen, Yong-Jun [1 ]
机构：
[1] Chinese Acad Sci, Inst Chem, CAS Key Lab Mol Recognit & Funct, BNLMS, Beijing 100190, Peoples R China
来源：
TETRAHEDRON-ASYMMETRY | 2010年 / 21卷 / 23期
基金：
中国国家自然科学基金;
关键词：
ENANTIOSELECTIVE ALPHA-AMINOXYLATION; CONJUGATE ADDITION; ORGANIC CATALYSTS; ALDEHYDES; PROLINE; OXIDATION; KETONES; HYDROXYAMINATION; AMINOOXYLATION; SULFONAMIDE;
D O I：
10.1016/j.tetasy.2010.11.002
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
An organocatalytic enantioselective N-nitroso-aldol reaction of 2-oxindoles promoted by a cinchona alkaloid catalyst has been developed. The reaction shows exclusively N-selectivity, affording corresponding products with good to excellent yields (up to 100%) and moderate enantioselectivity. The regioselectivity of nitroso-aldol reaction being controlled by different cinchona catalysts was also observed. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2800 / 2806
页数：7
相关论文
共 50 条
  • [1] Organocatalytic asymmetric nitroso aldol reaction of α-substituted malonamates
    Gupta, Ekta
    Vaishanv, Narendra Kumar
    Kumar, Sandeep
    Purshottam, Raja Krishnan
    Kant, Ruchir
    Mohanan, Kishor
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2022, 18 : 217 - 224
  • [2] Organocatalytic asymmetric aldol reaction in the presence of water
    Gryko, Dorota
    Saletra, Wojciech J.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (13) : 2148 - 2153
  • [3] Recent Advances on Asymmetric Nitroso Aldol Reaction
    Merino, Pedro
    Tejero, Tomas
    Delso, Ignacio
    Matute, Rosa
    SYNTHESIS-STUTTGART, 2016, 48 (05): : 653 - 676
  • [4] Organocatalytic chiral polymeric nanoparticles for asymmetric aldol reaction
    Abuaf, Meir
    Das, Subhomoy
    Mastai, Yitzhak
    RSC ADVANCES, 2023, 13 (03) : 1580 - 1586
  • [5] Aminohydroxyacetone synthons: versatile intermediates for the organocatalytic asymmetric aldol reaction
    Komatsu, Yoshiyuki
    Watanabe, Riki
    Ikishima, Hideaki
    Nakano, Keiji
    Ichikawa, Yoshiyasu
    Kotsuki, Hiyoshizo
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (15) : 2993 - 3001
  • [6] A highly efficient asymmetric organocatalytic aldol reaction in a ball mill
    Rodriguez, Belen
    Bruckmann, Angelika
    Bolm, Carsten
    CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (17) : 4710 - 4722
  • [7] Asymmetric Organocatalytic Electrophilic Heterofunctionalization of Oxindoles
    Freckleton, Megan
    Baeza, Alejandro
    Benavent, Llorenc
    Chinchilla, Rafael
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (06) : 1006 - 1014
  • [8] Unraveling and Manipulating the Stereospecific Retro-Aldol Reaction in the Organocatalytic Asymmetric Aldol Reaction of Isatin and Cyclohexanone
    Wang, Jing
    Deng, Zhi-Xiong
    Wang, Chao-Ming
    Xia, Peng-Ju
    Xiao, Jun-An
    Xiang, Hao-Yue
    Chen, Xiao-Qing
    Yang, Hua
    ORGANIC LETTERS, 2018, 20 (23) : 7535 - 7538
  • [9] Asymmetric Vinylogous Aldol Reaction of α-ketoesters with 3-alkylidene oxindoles
    Kumar, Krishna
    Jaiswal, Manish K.
    Singh, Ravi P.
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (23) : 4136 - 4140
  • [10] The synthesis of pharmacologically important oxindoles via the asymmetric aldol reaction of isatin and the investigation of the organocatalytic activity of new alicyclic β-amino acid derivatives
    Farago, Tuende
    Remete, Attila M. M.
    Szatmari, Istvan
    Ambrus, Rita
    Palko, Marta
    RSC ADVANCES, 2023, 13 (28) : 19356 - 19365
12345