Palladium-Catalyzed Asymmetric Ring Opening Reaction of Azabenzonorbornadienes with Aromatic Amines

被引:40
|
作者
Lu, Zhiwu [1 ]
Wang, Jun [2 ]
Han, Baiqiu [1 ]
Li, Sifeng [2 ]
Zhou, Yongyun [1 ]
Fan, Baomin [1 ,3 ]
机构
[1] Yunnan Minzu Univ, YMU HKBU Joint Lab Tradit Nat Med, Kunming 650500, Peoples R China
[2] South Univ Sci & Technol China, Dept Chem, Shenzhen 518055, Guangdong, Peoples R China
[3] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
基金
中国国家自然科学基金;
关键词
amines; asymmetric ring opening reaction; azabenzonorbornadienes; palladium; silver; N-BOC-AZABENZONORBORNADIENE; SUBSTITUTED PIPERAZINE NUCLEOPHILES; ENANTIOSELECTIVE EPOXIDATION; AZABICYCLIC ALKENES; OXABENZONORBORNADIENES; LIGANDS; ANALOGS;
D O I
10.1002/adsc.201500530
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A palladium/(R)-Binap catalyst for asymmetric ring opening reaction of azabenzonorbornadienes with amines was developed that afforded the corresponding substituted dihydronaphthalenes in good yields (up to 97%) with excellent enantioselectivities (up to > 99% ee). To the best of our knowledge, this represents the first palladium-catalyzed asymmetric ring opening reaction of azabenzonorbornadienes with heteronucleophiles.
引用
收藏
页码:3121 / 3125
页数:5
相关论文
共 50 条
  • [31] Palladium-catalyzed enantioselective ring opening of oxabicyclic alkenes with organozinc halides
    Li, M
    Yan, XX
    Hong, W
    Zhu, XZ
    Cao, BX
    Sun, J
    Hou, XL
    ORGANIC LETTERS, 2004, 6 (16) : 2833 - 2835
  • [32] Palladium-Catalyzed Ring-Opening Coupling of Cyclobutenols with Aryl Halides
    Matsuda, Takanori
    Matsumoto, Takeshi
    Murakami, Akira
    SYNLETT, 2018, 29 (06) : 754 - 758
  • [33] Palladium-Catalyzed Aromatic Azidocarbonylation
    Miloserdov, Fedor M.
    Grushin, Vladimir V.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (15) : 3668 - 3672
  • [34] Palladium-catalyzed ring opening of norbornene: efficient synthesis of methylenecyclopentane derivatives
    Wu, Xin-Xing
    Shen, Yi
    Chen, Wen-Long
    Chen, Si
    Hao, Xin-Hua
    Xia, Yu
    Xu, Peng-Fei
    Liang, Yong-Min
    CHEMICAL COMMUNICATIONS, 2015, 51 (38) : 8031 - 8033
  • [35] Tantalum (V) Chloride catalyzed ring opening of aziridines with aromatic amines
    Chandrasekhar, S
    Prakash, SJ
    Shyamsunder, T
    Ramachandar, T
    SYNTHETIC COMMUNICATIONS, 2004, 34 (21) : 3865 - 3873
  • [36] Zirconium(IV) chloride catalyzed ring opening of epoxides with aromatic amines
    Swamy, NR
    Goud, TV
    Reddy, SM
    Krishnaiah, P
    Venkateswarlu, Y
    SYNTHETIC COMMUNICATIONS, 2004, 34 (04) : 727 - 734
  • [37] Iridium-Catalyzed Asymmetric Ring Opening of Azabicyclic Alkenes by Amines
    Long, Yuhua
    Yang, Dingqiao
    Zhang, Zhenming
    Wu, Yujuan
    Zeng, Heping
    Chen, Yu
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (21): : 7291 - 7299
  • [38] Palladium-catalyzed ring contraction reaction of naphthoquinones upon reaction with alkynes
    Wang, Lei
    Zhang, Jianwei
    Lang, Ming
    Wang, Jian
    ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (05): : 603 - 608
  • [39] Iridium-Catalyzed Anti-Stereocontrolled Asymmetric Ring Opening of Azabicyclic Alkenes with Primary Aromatic Amines
    Yang, Dingqiao
    Long, Yuhua
    Wu, Yujuan
    Zuo, Xiongjun
    Tu, Qingqiang
    Fang, Shai
    Jiang, Lasheng
    Wang, Sanyong
    Li, Chunrong
    ORGANOMETALLICS, 2010, 29 (22) : 5936 - 5940
  • [40] Recent Developments in Palladium-Catalyzed Asymmetric Intermolecular Heck Reaction
    Li Hao
    Ding Changhua
    Xu Bin
    Hou Xuelong
    ACTA CHIMICA SINICA, 2014, 72 (07) : 765 - 770