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
  • [1] Organocatalytic Asymmetric Synthesis of Substituted 3-Hydroxy-2-oxindoles via Morita-Baylis-Hillman Reaction
    Liu, Yun-Lin
    Wang, Bo-Lun
    Cao, Jun-Jie
    Chen, Long
    Zhang, Yong-Xue
    Wang, Chao
    Zhou, Jian
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (43) : 15176 - 15178
  • [2] Chiral phosphine-squaramides as enantioselective catalysts for the intramolecular Morita-Baylis-Hillman reaction
    Song, Hong-Liang
    Yuan, Kui
    Wu, Xin-Yan
    CHEMICAL COMMUNICATIONS, 2011, 47 (03) : 1012 - 1014
  • [3] Catalytic asymmetric synthesis of 3-hydroxyl-2-oxindoles via enantioselective Morita-Baylis-Hillman reaction of isatins
    Wang, Ci-Ci
    Wu, Xin-Yan
    TETRAHEDRON, 2011, 67 (16) : 2974 - 2978
  • [4] Organocatalytic Enantioselective Morita-Baylis-Hillman Reaction of Maleimides with Isatins
    Chauhan, Pankaj
    Chimni, Swapandeep Singh
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2 (07) : 586 - 592
  • [5] Creation of bispiro[pyrazolone-3,3′-oxindoles] via a phosphine-catalyzed enantioselective [3+2] annulation of the Morita-Baylis-Hillman carbonates with pyrazoloneyldiene oxindoles
    Zhang, Jing
    Chan, Wai-Lun
    Chen, Ligong
    Ullah, Nisar
    Lu, Yixin
    ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (13) : 2210 - 2214
  • [6] Application of 7-azaisatins in enantioselective Morita-Baylis-Hillman reaction
    He, Qing
    Zhan, Gu
    Du, Wei
    Chen, Ying-Chun
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2016, 12 : 309 - 313
  • [7] Lewis-Base-Catalyzed Asymmetric [3+3] Annulation Reaction of Morita-Baylis-Hillman Carbonates: Enantioselective Synthesis of Spirocyclohexenes
    Yang, Wenjun
    Sun, Wei
    Zhang, Cheng
    Wang, Qijun
    Guo, Zhenyan
    Mao, Biming
    Liao, Jianning
    Guo, Hongchao
    ACS CATALYSIS, 2017, 7 (05): : 3142 - 3146
  • [8] Synthesis of 3-(γ, δ-Disubstituted)allylidene-2-Oxindoles from Isatins by Wittig Reaction with Morita-Baylis-Hillman Bromides
    Moon, Hye Ran
    Kim, Ko Hoon
    Lee, Junseong
    Kim, Jae Nyoung
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2015, 36 (01): : 219 - 225
  • [9] Synthesis of β-Lactams via Enantioselective Allylation of Anilines with Morita-Baylis-Hillman Carbonates
    Zi, You
    Lange, Markus
    Schueler, Philipp
    Krieck, Sven
    Westerhausen, Matthias
    Vilotijevic, Ivan
    SYNLETT, 2020, 31 (06) : 575 - 580
  • [10] Lewis Base Catalyzed Enantioselective Allylic Hydroxylation of Morita-Baylis-Hillman Carbonates with Water
    Zhu, Bo
    Yan, Lin
    Pan, Yuanhang
    Lee, Richmond
    Liu, Hongjun
    Han, Zhiqiang
    Huang, Kuo-Wei
    Tan, Choon-Hong
    Jiang, Zhiyong
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (16) : 6894 - 6900
12345