Organocatalytic Enantioselective Decarboxylative Addition of Malonic Acids Half Thioesters to Isatins

被引:101
|
作者
Hara, Noriyuki [1 ]
Nakamura, Shuichi [1 ]
Funahashi, Yasuhiro [1 ]
Shibata, Norio [1 ]
机构
[1] Nagoya Inst Technol, Dept Frontier Mat, Grad Sch Engn, Showa Ku, Nagoya, Aichi 4668555, Japan
关键词
aldol reaction; decarboxylative addition; enantioselectivity; organic catalysis; ASYMMETRIC ALDOL CONDENSATION; 1ST TOTAL-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; SQUARAMIDE DERIVATIVES; (R)-CONVOLUTAMYDINE; SULFONYLIMINES; ACETALDEHYDE; ALKALOIDS; KETONES;
D O I
10.1002/adsc.201100410
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The organocatalytic enantioselective decarboxylative addition of malonic acids half thioesters to isatins using a squaramide catalyst afforded the products with high enantioselectivity. These products are key intermediates in the synthesis of 3-substituted 3-hydroxy-2-oxindole derivatives. The first enantioselective synthesis of (-)-flustraminol B has been accomplished.
引用
收藏
页码:2976 / 2980
页数:5
相关论文
共 50 条
  • [41] Enantioselective organocatalytic conjugate addition of organoboron nucleophiles
    Nguyen, Truong N.
    May, Jeremy A.
    TETRAHEDRON LETTERS, 2017, 58 (16) : 1535 - 1544
  • [42] Enantioselective Organocatalytic Michael Addition of Aldehydes to β-Nitrostyrenes
    Laars, Marju
    Ausmees, Kerti
    Uudsemaa, Merle
    Tamm, Toomas
    Kanger, Tonis
    Lopp, Margus
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (10): : 3772 - 3775
  • [43] Enantioselective Organocatalytic Conjugate Addition of Alkenes to α,β-Enones
    Cui, Lingyun
    Zhang, Long
    Luo, Sanzhong
    Cheng, Jin-Pei
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (17) : 3540 - 3545
  • [44] Organocatalytic enantioselective conjugate addition of aldehydes to maleimides
    Zhao, Gui-Ling
    Xu, Yongmei
    Sunden, Henrik
    Eriksson, Lars
    Sayah, Mahmoud
    Cordova, Armando
    CHEMICAL COMMUNICATIONS, 2007, (07) : 734 - 735
  • [45] Enantioselective Organocatalytic Michael Addition of Anthrone to Nitroalkenes
    He, Tianxiong
    Wu, Xinyan
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2010, 30 (09) : 1400 - 1404
  • [46] Organocatalytic, enantioselective conjugate addition of nitroalkanes to nitroolefins
    Wang, Jian
    Li, Hao
    Zua, Liansuo
    Jiang, Wei
    Wang, Wei
    ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (15) : 2047 - 2050
  • [47] Enantioselective Organocatalytic Michael Addition of Cyclobutanones to Nitroalkenes
    Mailhol, Damien
    Duque, Maria del Mar Sanchez
    Raimondi, Wilfried
    Bonne, Damien
    Constantieux, Thierry
    Coquerel, Yoann
    Rodriguez, Jean
    ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (18) : 3523 - 3532
  • [48] Enantioselective organocatalytic double Michael addition reactions
    Li, Hao
    Zu, Liansuo
    Xie, Hexin
    Wang, Jian
    Jiang, Wei
    Wang, Wei
    ORGANIC LETTERS, 2007, 9 (09) : 1833 - 1835
  • [49] Decarboxylative Mannich Reactions with Substituted Malonic Acid Half-Oxyesters
    Xavier, Tania
    Condon, Sylvie
    Pichon, Christophe
    Le Gall, Erwan
    Presset, Marc
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (08): : 5452 - 5462
  • [50] Malonic Acid Half Thioesters (MAHTs) as Efficient Enolate Precursors in Biomimetic Catalysis
    Bae, Han Yong
    SYNLETT, 2015, 26 (05) : 705 - 706