Palladium-catalyzed asymmetric allylic alkylation of 3-amino-2-oxindoles: Synthesis of 3-allyl-3-amino-2-oxindoles

被引：4
作者：
Kumarswamyreddy, Nandarapu [1 ,2 ]
Jayakumar, Samydurai [1 ]
Kesavan, Venkitasamy [1 ]
机构：
[1] Indian Inst Technol Madras, Bhupat & Jyothi Metha Sch Biosci, Dept Biotechnol, Chem Biol Lab, Chennai 600036, Tamil Nadu, India
[2] Indian Inst Technol Tirupati, Dept Chem, Tirupati 517506, Andhra Pradesh, India
来源：
TETRAHEDRON LETTERS | 2021年 / 82卷
关键词：
3-Ally-3-amino oxindoles; Asymmetric allylic alkylation; Palladium catalyst; Bi(oxazoline) ligands; Spiropyrrolidine oxindoles; ENANTIOSELECTIVE SYNTHESIS; EFFICIENT SYNTHESIS; 3+2 CYCLOADDITION; 1,3-DIPOLAR CYCLOADDITION; AZOMETHINE YLIDES; MANNICH REACTION; QUATERNARY; ALLYLATION; OXINDOLES; ISATIN;
D O I：
10.1016/j.tetlet.2021.153385
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Tartrate derived bi(oxazoline) ligand with palladium (II) species catalyzed asymmetric allylic alkylation reaction to access highly valuable 3-allyl-3-amino-2-oxindoles with vicinal quaternary and tertiary stereocenters in very good yields (up to 91%) and excellent enantioselectivity (up to 98% ee) with moderate to good diastereoselectivity (up to 5:1). The synthetic utility of 3-allyl-3-amino-2-oxindole was further demonstrated to construct spiro(oxindole-3,2'-pyrrolidine) with consecutive one quaternary and three tertiary chiral centers in good stereoselectivity (dr = 8:1 and 80% ee) through metal-free intramolecular iodocyclization reaction. (C) 2021 Elsevier Ltd. All rights reserved.
引用
收藏
页数：6
相关论文
共 50 条
  • [31] Synthesis of Enantioenriched 3-Amino-3-Substituted Oxindoles by Stereoselective Mannich Reaction Catalyzed by Supported Bifunctional Thioureas.
    Rodriguez-Ferrer, Patricia
    Sanz-Novo, Miguel
    Maestro, Alicia
    Andres, Jose M.
    Pedrosa, Rafael
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (15) : 3645 - 3655
  • [32] Palladium-Catalyzed Asymmetric Allylic Alkylation of 3-Aryloxindoles with Allylidene Dipivalate: A Useful Enol Pivalate Product
    Trost, Barry M.
    Masters, James T.
    Burns, Aaron C.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (08) : 2260 - 2264
  • [33] Palladium-catalyzed asymmetric allylic alkylation of acyclic ketones for synthesis of 2,2-disubsituted pyrrolidine derivatives
    Lian, Wen-Fang
    Wang, Cui-Cui
    Kang, Huai-Ping
    Li, Hai-Ling
    Feng, Juan
    Liu, Shouxin
    Zhang, Zhi-Wei
    TETRAHEDRON LETTERS, 2017, 58 (14) : 1399 - 1402
  • [34] Synthesis of 3-substituted 2-oxindoles from secondary α-bromo-propionanilides via palladium-catalyzed intramolecular cyclization
    Shen, Hui
    Du, Yu
    Kan, Jian
    Su, Weiping
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (17) : 3589 - 3597
  • [35] Iridium-catalyzed asymmetric hydrogenation of 3-substituted unsaturated oxindoles to prepare C3-mono substituted oxindoles
    Liu, Yuanyuan
    Yao, Dongmei
    Li, Kun
    Tian, Fengtao
    Xie, Fang
    Zhang, Wanbin
    TETRAHEDRON, 2011, 67 (44) : 8445 - 8450
  • [36] Construction of Enantioenriched Quaternary C-Cl Oxindoles through Palladium-Catalyzed Asymmetric Allylic Substitution with Chloroenolates
    Huang, Wen
    Yang, Jingjie
    Gao, Kai
    Wang, Zhiming
    Huang, Guobo
    Yao, Weijun
    Yang, Jianguo
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (21) : 15298 - 15310
  • [37] Palladium-catalyzed oxidative arylation of trisubstituted olefin: an efficient synthesis of 3-(disubstituted)alkylidene-oxindoles
    Lee, Hyun Ju
    Kim, Ko Hoon
    Kim, Se Hee
    Kim, Jae Nyoung
    TETRAHEDRON LETTERS, 2013, 54 (02) : 170 - 175
  • [38] 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
  • [39] Catalytic Asymmetric Alkylation of 3-Aryl- Substituted Oxindoles to give 3,3-Disubstituted Oxindoles under Phase- Transfer Conditions
    Deng, Fei
    Moteki, Shin A.
    Maruoka, Keiji
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 3 (04) : 395 - 398
  • [40] Divergent Synthesis of 3,3-Disubstituted Oxindoles Initiated by Palladium-Catalyzed Intramolecular Arylation of Unsaturated Amides
    Wei, Fang
    Wei, Lei
    Zhou, Ling
    Tung, Chen-Ho
    Ma, Yudao
    Xu, Zhenghu
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (08) : 971 - 975
12345