Chiral phosphine-squaramide-catalyzed Morita-Baylis-Hillman reaction: enantioselective synthesis of 3-hydroxy-2-oxindoles

被引：42
|
作者：
Qian, Jing-Ying [1 ,2 ]
Wang, Ci-Ci [1 ,2 ]
Sha, Feng [1 ,2 ]
Wu, Xin-Yan [1 ,2 ,3 ]
机构：
[1] E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China
[2] E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China
[3] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
来源：
RSC ADVANCES | 2012年 / 2卷 / 14期
基金：
中国国家自然科学基金;
关键词：
ORGANOCATALYTIC ASYMMETRIC-SYNTHESIS; ALDOL REACTIONS; ISATINS; ALLYLATION; OXINDOLES; ALCOHOLS; INDOLES; DESIGN; (R)-CONVOLUTAMYDINE; HYDROXYLATION;
D O I：
10.1039/c2ra20521a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Phosphine-squaramide derivatives were developed to catalyze the enantioselective Morita-Baylis-Hillman reaction of acrylates with isatins to construct 3-hydroxy-2-oxindoles with quaternary stereocenters. In the presence of 2 mol% H-bonding catalyst 3e, the desired products were achieved in high yields and good-to-excellent enantioselectivities (up to 95% ee).
引用
收藏
页码：6042 / 6048
页数：7
相关论文
共 50 条
  • [31] Chiral thiourea derivatives as organocatalyts in the enantioselective Morita-Baylis-Hillman reactions
    Aydin, A. Ebru
    ARKIVOC, 2020, : 21 - 38
  • [32] Annulative Morita-Baylis-Hillman reaction to synthesise chiral dibenzocycloheptanes
    Mondal, Atanu
    Shivangi
    Tung, Pinku
    Wagulde, Siddhant, V
    Ramasastry, S. S., V
    CHEMICAL COMMUNICATIONS, 2021, 57 (73) : 9260 - 9263
  • [33] Phosphine-Catalyzed Enantioselective [4+2] Cycloaddition-Semipinacol-Type-Rearrangement Reaction of Morita-Baylis-Hillman Carbonates
    Zhong, Yuan
    Zhao, Xiaoyun
    Gan, Lu
    Hong, Sihua
    Jiang, Xianxing
    ORGANIC LETTERS, 2018, 20 (14) : 4250 - 4254
  • [34] Synthesis, Characterization and Catalytic Properties of Chiral BINOL Functionalized Mesoporous Silicas for Enantioselective Morita-Baylis-Hillman Reaction
    Xiaomei Wang
    Peng Han
    Xuepeng Qiu
    Xiangling Ji
    Lianxun Gao
    Catalysis Letters, 2008, 124 : 418 - 427
  • [35] Synthesis, characterization and catalytic properties of chiral BINOL functionalized mesoporous silicas for enantioselective Morita-Baylis-Hillman reaction
    Wang, Xiaomei
    Han, Peng
    Qiu, Xuepeng
    Ji, Xiangling
    Gao, Lianxun
    CATALYSIS LETTERS, 2008, 124 (3-4) : 418 - 427
  • [36] Asymmetric Morita-Baylis-Hillman reactions catalyzed by chiral Bronsted acids
    McDougal, NT
    Schaus, SE
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (40) : 12094 - 12095
  • [37] Chiral multifunctional thiourea-phosphine catalyzed asymmetric [3+2] annulation of Morita-Baylis-Hillman carbonates with maleimides
    Deng, Hong-Ping
    Wang, De
    Wei, Yin
    Shi, Min
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2012, 8 : 1098 - 1104
  • [38] Chiral DMAP catalyzed allylic amination of Morita-Baylis-Hillman carbonates
    Ma, Gaoyuan
    Sibi, Mukund
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [39] The enantioselective intramolecular Morita-Baylis-Hillman reaction catalyzed by amino acid-derived phosphinothiourea
    Gong, Jing-Jing
    Yuan, Kui
    Song, Hong-Liang
    Wu, Xin-Yan
    TETRAHEDRON, 2010, 66 (13) : 2439 - 2443
  • [40] Dual catalyst control in the enantioselective intramolecular Morita-Baylis-Hillman reaction
    Aroyan, CE
    Vasbinder, MM
    Miller, SJ
    ORGANIC LETTERS, 2005, 7 (18) : 3849 - 3851
12345