Chiral iminophosphoranes organocatalyzed asymmetric hydroxylation of 3-substituted oxindoles with oxaziridines

被引：15
|
作者：
Li, Baocheng [1 ,2 ]
Xu, Zhen-Jiang [1 ,2 ]
Han, Jianwei [1 ,2 ,3 ]
机构：
[1] Shanghai Inst Technol, Sch Chem & Environm Engn, 100 Haiquan Rd, Shanghai 201418, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai Hong Kong Joint Lab Chem Synth, 345 Ling Ling Rd, Shanghai 200032, Peoples R China
[3] East China Univ Sci & Technol, Sch Chem & Mol Engn, Inst Fine Chem, Key Lab Adv Mat, 130 Meilong Rd, Shanghai 200237, Peoples R China
来源：
TETRAHEDRON LETTERS | 2018年 / 59卷 / 25期
基金：
中国国家自然科学基金;
关键词：
Organocatalysis; Superbase; Iminophosphorane; Oxindoles; Hydroxylation; ENANTIOSELECTIVE ALPHA-HYDROXYLATION; BETA-KETO-ESTERS; PHASE-TRANSFER CATALYSTS; DICARBONYL COMPOUNDS; MICHAEL ADDITION; MOLECULAR-OXYGEN; DERIVATIVES; 3-HYDROXYOXINDOLE;
D O I：
10.1016/j.tetlet.2018.05.018
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Enantioselective hydroxylation of N-protected 3-substituted oxindoles has been developed via chiral iminophosphorane catalysis with oxaziridines as oxidants. As such, a variety of optically active 3-substituted-3-hydroxy-2-oxindoles were obtained in excellent yields (91-99%) and moderate to excellent level of enantiomeric excess (up to 94% ee). (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2412 / 2417
页数：6
相关论文
共 50 条
  • [31] Asymmetric Substitution at the Tetrasubstituted Chiral Carbon: Catalytic Ring-Opening Alkylation of Racemic 2,2-Disubstituted Aziridines with 3-Substituted Oxindoles
    Ohmatsu, Kohsuke
    Ando, Yuichiro
    Ooi, Takashi
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (50) : 18706 - 18709
  • [32] Organocatalytic Michael addition of unprotected 3-substituted oxindoles to nitroolefins
    Ding, Miao
    Zhou, Feng
    Qian, Zi-Qing
    Zhou, Jian
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (13) : 2912 - 2914
  • [33] Asymmetric synthesis of 3-substituted γ- and δ-sultams
    Enders, D
    Moll, A
    Bats, JW
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (05) : 1271 - 1284
  • [34] Organocatalytic Enantioselective Stereoablative Hydroxylation of 3-Halooxindoles: An Effective Method for the Construction of Enantioenriched 3-Substituted 3-Hydroxy-2-Oxindoles
    Liao, Yu-Hua
    Wu, Zhi-Jun
    Han, Wen-Yong
    Zhang, Xiao-Mei
    Yuan, Wei-Cheng
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (29) : 8916 - 8920
  • [35] Chiral Scandium(III)-Catalyzed Enantioselective α-Arylation of N-Unprotected 3-Substituted Oxindoles with Diaryliodonium Salts
    Guo, Jing
    Dong, Shunxi
    Zhang, Yulong
    Kuang, Yulong
    Liu, Xiaohua
    Lin, Lili
    Feng, Xiaoming
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (39) : 10245 - 10249
  • [36] Chiral Bronsted acid-catalyzed asymmetric transformations of 3-substituted 3-hydroxyisoindolinones
    Gredicak, Matija
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256
  • [37] Synthesis and Application of 3-Substituted (S)-BINOL as Chiral Ligands for the Asymmetric Ethylation of Aldehydes
    Zhang, Zhi-Guang
    Dong, Zhi-Bing
    Li, Jin-Shan
    CHIRALITY, 2010, 22 (09) : 820 - 826
  • [38] Scandium-Catalyzed Asymmetric 1,6-Addition of 3-Substituted Oxindoles to Linear Dienyl Ketones
    Wang, Zhen
    Kang, Tengfei
    Yao, Qian
    Ji, Jie
    Liu, Xiaohua
    Lin, Lili
    Feng, Xiaoming
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (21) : 7709 - 7712
  • [39] Highly enantioselective synthesis of chiral 3-substituted indolines by catalytic asymmetric hydrogenation of indoles
    Kuwano, R
    Kaneda, K
    Ito, T
    Sato, K
    Kurokawa, T
    Ito, Y
    ORGANIC LETTERS, 2004, 6 (13) : 2213 - 2215
  • [40] A facile synthesis and asymmetric catalytic activity of new 3-substituted chiral BINOL ligands
    Liu, Bing
    Fang, Cao
    Dong, Zhi-Bing
    Li, Jin-Shan
    APPLIED ORGANOMETALLIC CHEMISTRY, 2008, 22 (01) : 55 - 58
12345