Catalytic asymmetric synthesis of 3-hydroxyl-2-oxindoles via enantioselective Morita-Baylis-Hillman reaction of isatins

被引：43
|
作者：
Wang, Ci-Ci
Wu, Xin-Yan [1 ]
机构：
[1] E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China
来源：
TETRAHEDRON | 2011年 / 67卷 / 16期
基金：
中国国家自然科学基金;
关键词：
Enantioselective organocatalysis; Morita-Baylis-Hillman reaction; Bifunctional phosphinothiourea; Isatin; 3-Hydroxyl-2-oxindole; ARYLBORONIC ACIDS; ADDUCTS; DERIVATIVES; PHOSPHINOTHIOUREA; OXINDOLES; ALDEHYDES; (R)-CONVOLUTAMYDINE; CONSTRUCTION; ALLYLATION; ALKALOIDS;
D O I：
10.1016/j.tet.2011.02.045
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The enantioselective Morita-Baylis-Hillman reaction of acrylates to isatins was investigated for the first time, employing bifunctional phosphinothiourea organocatalysts based on chiral cyclohexane scaffold. The 3-hydroxyl-2-oxindole derivatives were obtained in excellent yields with moderate enantioselectivity (up to 69% ee) in the presence of 10 mol % catalyst 1b. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2974 / 2978
页数：5
相关论文
共 50 条
  • [1] 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
  • [2] Enantioselective Morita-Baylis-Hillman Reaction of Isatins with Acrylates: Facile Creation of 3-Hydroxy-2-oxindoles
    Zhong, Fangrui
    Chen, Guo-Ying
    Lu, Yixin
    ORGANIC LETTERS, 2011, 13 (01) : 82 - 85
  • [3] Asymmetric Morita-Baylis-Hillman reaction of isatins with α,β-unsaturated γ-butyrolactam as the nucleophile
    Duan, Zhiqiang
    Zhang, Zirui
    Qian, Ping
    Han, Jianlin
    Pan, Yi
    RSC ADVANCES, 2013, 3 (26): : 10127 - 10130
  • [4] 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
  • [5] Aqueous Morita-Baylis-Hillman Reaction of Unprotected Isatins with Cyclic Enones
    Gomes, Juliana C.
    Sirvent, Jordi
    Moyano, Albert
    Rodrigues, Manoel T., Jr.
    Coelho, Fernando
    ORGANIC LETTERS, 2013, 15 (22) : 5838 - 5841
  • [6] Chiral phosphine-squaramide-catalyzed Morita-Baylis-Hillman reaction: enantioselective synthesis of 3-hydroxy-2-oxindoles
    Qian, Jing-Ying
    Wang, Ci-Ci
    Sha, Feng
    Wu, Xin-Yan
    RSC ADVANCES, 2012, 2 (14) : 6042 - 6048
  • [7] 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
  • [8] Enantioselective Synthesis of β-Iodo Morita-Baylis-Hillman Esters by a Catalytic Asymmetric Three-Component Coupling Reaction
    Senapati, Bidyut Kumar
    Hwang, Geum-Sook
    Lee, Sungil
    Ryu, Do Hyun
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (24) : 4398 - 4401
  • [9] Privileged chiral catalysts in asymmetric Morita-Baylis-Hillman/aza-Morita-Baylis-Hillman reaction
    Wei Yin
    Shi Min
    CHINESE SCIENCE BULLETIN, 2010, 55 (17): : 1699 - 1711
  • [10] 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
12345