Enantioselective Alkynylation of 2-Aryl-3H-indol-3-ones via Cooperative Catalysis of Copper/Chiral Phosphoric Acid

被引：3
|
作者：
Wu, Xi-Xi [1 ]
Ma, Tao [1 ]
Qiao, Xiu-Xiu [1 ]
Zou, Chang-Peng [1 ]
Li, Ganpeng [1 ]
He, Yonghui [1 ]
Zhao, Xiao-Jing [1 ]
机构：
[1] Yunnan Minzu Univ, Sch Ethn Med, Key Lab Chem Ethn Med Resources, Key Lab Nat Prod Synthet Biol Ethn Med Endophytes,, Kunming 650500, Peoples R China
来源：
CHEMISTRY-AN ASIAN JOURNAL | 2023年 / 18卷 / 18期
基金：
中国国家自然科学基金;
关键词：
Chiral phosphoric acids; Cooperative catalysis; 2-Aryl-3H-indol-3-ones; C2-quaternary indolin-3-ones; Chiral propargylic aminles; ORGANOCATALYTIC ASYMMETRIC-SYNTHESIS; BRONSTED ACID; METAL CATALYSIS; IMINES; CYCLIZATION; ALKALOIDS; KETIMINES;
D O I：
10.1002/asia.202300526
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A facile enantioselective alkynylation of cyclic ketimines attached to a neutral functional group utilizing the dual Cu(I)-CPA catalysis is described. The strategy of the alkynylation of 2-aryl-3H-indol-3-one directly to chiral propargylic amines containing indolin-3-one moiety in good yields and enantioselectivities. Moreover, gram-scale synthesis of chiral propargylamines based C2-quaternary indolin-3-ones was performed. The synthetic applications were confirmed by transformations of the products with no decrease in the yield and enantioselectivity.
引用
收藏
页数：5
相关论文
共 50 条
  • [1] Chiral Phosphoric Acid Catalyzed Asymmetric Mannich Reaction of 2-Aryl-3H-indol-3-ones with α-H Diazoacetates
    Lin, Cheng
    He, Jia-Hao
    Rao, Ming-Liang
    Yang, Gui-Ping
    Li, Wen-Jie
    Zhou, Meng
    Zhao, Chong
    Fu, Xiao-Zhong
    He, Bin
    Zhao, Yong-Long
    ORGANIC LETTERS, 2025,
  • [2] Chiral phosphoric acid-catalyzed enantioselective aza-Friedel-Crafts reaction of naphthols and electron-rich phenols with 2-aryl-3H-indol-3-ones
    Ma, Tao
    He, Yonghui
    Qiao, Xiu-Xiu
    Zou, Chang-Peng
    Wu, Xi-Xi
    Li, Ganpeng
    Zhao, Xiao-Jing
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (03) : 489 - 493
  • [3] Study of the addition of Grignard reagents to 2-aryl-3H-indol-3-ones
    Liu, Y
    McWhorter, WW
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (07): : 2618 - 2622
  • [4] FACILE SYNTHESIS OF 2-ARYL-3H-INDOL-3-ONES VIA SINGLET OXYGENATION OF 2-ARYLINDOLES
    LING, KQ
    SYNTHETIC COMMUNICATIONS, 1995, 25 (23) : 3831 - 3835
  • [5] B(C6F5)3/Chiral Phosphoric Acid Catalyzed Ketimine-Ene Reaction of 2-Aryl-3H-indol-3-ones and α-Methylstyrenes
    Zhang, Qing-Xia
    Li, Yao
    Wang, Jie
    Yang, Chen
    Liu, Cheng-Jun
    Li, Xin
    Cheng, Jin-Pei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (11) : 4550 - 4556
  • [6] 2-Aryl-3H-indol-3-ones: Synthesis, electrochemical behaviour and antiplasmodial activities
    Najahi, Ennaji
    Valentin, Alexis
    Fabre, Paul-Louis
    Reybier, Karine
    Nepveu, Francoise
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 78 : 269 - 274
  • [7] Synthesis of 2-aryl-3H-indol-3-ones via trapping reaction in singlet oxygenation of 2-arylindoles
    Ling, KQ
    CHINESE JOURNAL OF CHEMISTRY, 1996, 14 (03) : 259 - 264
  • [8] Synthesis of 2-aryl-3H-indol-3-ones via trapping reaction in singlet oxygenation of 2-arylindoles
    LING
    ChineseJournalofChemistry, 1996, (03) : 259 - 264
  • [9] Pd-Catalyzed Asymmetric Allylation Reaction of 2-Aryl-3H-indol-3-ones with Allyltrimethylsilane
    Yang, Fan
    Wang, Lun
    Liang, Meiqi
    Zhang, Linchun
    Fan, Baomin
    Yao, Bo
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (03): : 1873 - 1879
  • [10] Synthesis of Fluorine-Containing C2-Tetrasubstituted Indolin-3-ones via Rapid Incorporation of Difluoroacetate Radical Into 2-Aryl-3H-indol-3-ones
    Li, Qian
    Zhao, Shi-Na
    Li, Ganpeng
    He, Yonghui
    Zhao, Xiao-Jing
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (31)
12345