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
  • [21] Tartrate-derived iminophosphorane catalyzed asymmetric hydroxymethylation of 3-substituted oxindoles with paraformaldehyde
    Gao, Xing
    Han, Jianwei
    Wang, Limin
    ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (06): : 656 - 660
  • [22] Reductive aromatization of oxindoles to 3-substituted indoles
    Mandal, Tirtha
    Chakraborti, Gargi
    Dash, Jyotirmayee
    TETRAHEDRON LETTERS, 2020, 61 (28)
  • [23] Organocatalytic asymmetric Michael addition of unprotected 3-substituted oxindoles to 1,4-naphthoquinone
    Yu, Jin-Sheng
    Zhou, Feng
    Liu, Yun-Lin
    Zhou, Jian
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2012, 8 : 1360 - 1365
  • [24] Organocatalytic stereoselective Mannich reaction of 3-substituted oxindoles
    Tian, Xu
    Jiang, Kun
    Peng, Jing
    Du, Wei
    Chen, Ying-Chun
    ORGANIC LETTERS, 2008, 10 (16) : 3583 - 3586
  • [25] Enantioselective organocatalytic oxyamination of unprotected 3-substituted oxindoles
    Companyo, Xavier
    Valero, Guillem
    Pineda, Oriol
    Calvet, Teresa
    Font-Bardia, Merce
    Moyano, Albert
    Rios, Ramon
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (02) : 431 - 439
  • [26] HIGHLY STEREOSELECTIVE ADDITION OF ORGANOLITHIUM REAGENTS TO CHIRAL OXAZOLINES - ASYMMETRIC SYNTHESIS OF 3-SUBSTITUTED ALKANOIC ACIDS AND 3-SUBSTITUTED LACTONES
    MEYERS, AI
    SMITH, RK
    WHITTEN, CE
    JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (13): : 2250 - 2256
  • [27] Bicyclic-Guanidine-Catalyzed Asymmetric Michael Addition of 3-Substituted Oxindoles to 2-Cyclopentenone
    Yang, Caiyun
    Chen, Wenchao
    Yang, Wenguo
    Zhu, Bo
    Yan, Lin
    Tan, Choon-Hong
    Jiang, Zhiyong
    CHEMISTRY-AN ASIAN JOURNAL, 2013, 8 (12) : 2960 - 2964
  • [28] Highly Enantioselective Synthesis of 3-Amino-2-oxindole Derivatives: Catalytic Asymmetric α-Amination of 3-Substituted 2-Oxindoles with a Chiral Scandium Complex
    Yang, Zhigang
    Wang, Zhen
    Bai, Sha
    Shen, Ke
    Chen, Donghui
    Liu, Xiaohua
    Lin, Lili
    Feng, Xiaoming
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (22) : 6632 - 6637
  • [29] Laccase-catalyzed 3-Arylation of 3-Substituted Oxindoles
    Pietruszka, Joerg
    Wang, Chuan
    CHEMCATCHEM, 2012, 4 (06) : 782 - 785
  • [30] Synthesis of Chiral 3-Substituted 3-Amino-2-oxindoles through Enantioselective Catalytic Domino and Tandem Reactions
    Pellissier, Helene
    SYNTHESIS-STUTTGART, 2019, 51 (06): : 1311 - 1318
12345