Asymmetric Organocatalytic Synthesis of Spiro-cyclopropaneoxindoles

被引:21
作者
Noole, Artur [1 ]
Malkov, Andrei V. [2 ]
Kanger, Tonis [1 ]
机构
[1] Tallinn Univ Technol, Dept Chem, EE-12618 Tallinn, Estonia
[2] Univ Loughborough, Dept Chem, Loughborough LE11 3TU, Leics, England
来源
SYNTHESIS-STUTTGART | 2013年 / 45卷 / 18期
关键词
spiro compounds; organocatalysis; oxindoles; 3-chlorooxindoles; asymmetric synthesis; ENANTIOSELECTIVE CYCLOPROPANATION; OXINDOLES; SPIROOXINDOLES; CATALYSIS; CENTERS;
D O I
10.1055/s-0033-1338505
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Straightforward cascade reactions for the synthesis of spiro-cyclopropaneoxindoles are described. The target compounds are obtained in high yields and in good enantio- and diastereoselectivities via hydrogen bonding or iminium catalysis.
引用
收藏
页码:2520 / 2524
页数:5
相关论文
共 18 条
  • [1] Squaramides: Bridging from Molecular Recognition to Bifunctional Organocatalysis
    Aleman, Jose
    Parra, Alejandro
    Jiang, Hao
    Jorgensen, Karl Anker
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (25) : 6890 - 6899
  • [2] Strategies for the enantioselective synthesis of spirooxindoles
    Ball-Jones, Nicolas R.
    Badillo, Joseph J.
    Franz, Annaliese K.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (27) : 5165 - 5181
  • [3] Asymmetric catalysis with bifunctional cinchona alkaloid-based urea and thiourea organocatalysts
    Connon, Stephen J.
    [J]. CHEMICAL COMMUNICATIONS, 2008, (22) : 2499 - 2510
  • [4] Diastereodivergent Synthesis of 3-Spirocyclopropyl-2-oxindoles through Direct Enantioselective Cyclopropanation of Oxindoles
    Dou, Xiaowei
    Lu, Yixin
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (27) : 8315 - 8319
  • [5] Small-molecule H-bond donors in asymmetric catalysis
    Doyle, Abigail G.
    Jacobsen, Eric N.
    [J]. CHEMICAL REVIEWS, 2007, 107 (12) : 5713 - 5743
  • [6] He Y., 2004, [No title captured], Patent No. [WO2004/037247A1, 2004037247]
  • [7] Recent Advances in Asymmetric Organocatalytic Construction of 3,3′-Spirocyclic Oxindoles
    Hong, Liang
    Wang, Rui
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (06) : 1023 - 1052
  • [8] Jiang T, 2006, BIOORG MED CHEM LETT, V16, P2105, DOI 10.1016/j.bmcl.2006.01.073
  • [9] McGilvra J.D., 2007, Enantioselective Organocatalysis, P189
  • [10] 3-Chlorooxindoles: Versatile Starting Materials for Asymmetric Organocatalytic Synthesis of Spirooxindoles
    Noole, Artur
    Oseka, Maksim
    Pehk, Tonis
    Oeeren, Mario
    Jaerving, Ivar
    Elsegood, Mark R. J.
    Malkov, Andrei V.
    Lopp, Margus
    Kanger, Tonis
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (05) : 829 - 835