Silver-catalyzed dynamic systemic resolution of α-iminonitriles in a 1,3-dipolar cycloaddition process

被引:29
|
作者
Hu, Lei [1 ]
Ramstrom, Olof [1 ]
机构
[1] KTH Royal Inst Technol, Dept Chem, Stockholm, Sweden
基金
瑞典研究理事会;
关键词
COMBINATORIAL RESOLUTION; ASYMMETRIC-SYNTHESIS; INHIBITORS; INDOLIZIDINE; CHEMISTRY; LIBRARIES;
D O I
10.1039/c4cc00944d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A dynamic azomethine ylide system was established using Sc(OTf)(3) and Ag/Taniaphos as catalysts. The system was subsequently kinetically resolved in a tandem 1,3-dipolar cycloaddition process where the silver complex acted as both a reaction catalyst and an external selector, resulting in the formation of an exclusive pyrrolidine product in good yield and enantiopurity.
引用
收藏
页码:3792 / 3794
页数:3
相关论文
共 50 条
  • [1] Silver-Catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides with β-Boryl Acrylates
    Lopez-Perez, Ana
    Segler, Marwin
    Adrio, Javier
    Carretero, Juan C.
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (06): : 1945 - 1948
  • [2] Silver-Catalyzed Reaction of Enynals with Alkenes: A Tandem 1,3-Dipolar Cycloaddition/Cyclopropanation
    Liang, Renxiao
    Ma, Tongmei
    Zhu, Shifa
    ORGANIC LETTERS, 2014, 16 (17) : 4412 - 4415
  • [3] Catalytic Asymmetric 1,3-Dipolar Cycloaddition of α-Iminonitriles
    Robles-Machin, Rocio
    Alonso, Ines
    Adrio, Javier
    Carretero, Juan C.
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (18) : 5286 - 5291
  • [4] Diastereoselective Silver-Catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides with Fluorinated Imine
    Xie, Haibo
    Zhu, Jiangtao
    Chen, Zixian
    Li, Shan
    Wu, Yongming
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (21): : 7468 - 7471
  • [5] Silver-Catalyzed Diastereoselective Synthesis of Spirocyclic Pyrrolidine-Lactones by 1,3-Dipolar Cycloaddition
    Garcia-Minguens, Eduardo
    Caletkova, Ol'ga
    Berkes, Dusan
    Najera, Carmen
    Sansano, Jose M.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (34) : 5563 - 5571
  • [6] A Chiral Secondary Amine-Amidophosphane Precatalyst for Silver-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition Reactions
    Zheng, Xiaojun
    Deng, Qifu
    Hou, Qinglin
    Zhang, Kaiqiang
    Wen, Pushan
    Hu, Shunqin
    Wang, Haifei
    SYNTHESIS-STUTTGART, 2018, 50 (12): : 2347 - 2358
  • [7] Synthesis of Pyrrole via a Silver-Catalyzed 1,3-Dipolar Cycloaddition/Oxidative Dehydrogenative Aromatization Tandem Reaction
    Liu, Yan
    Hu, Huayou
    Wang, Xiang
    Zhi, Sanjun
    Kan, Yuhe
    Wang, Chao
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (08): : 4194 - 4202
  • [8] Catalytic Asymmetric 1,3-Dipolar Cycloaddition of α-Iminonitriles (vol 16, pg 5286, 2010)
    Robles-Machin, R.
    Alonso, I.
    Adrio, J.
    Carretero, J. C.
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (47) : CP43 - CP43
  • [9] Piperidine-Catalyzed 1,3-Dipolar Cycloaddition of Diazoesters to Enones
    Huang, Jiayao
    Wu, Minghu
    Hu, Liqiang
    Guo, Haibin
    Sun, Shaofa
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (04) : 462 - 465
  • [10] Silver/Segphos-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition for the Enantioselective Synthesis of Pyrrolidine Spirooxindoles
    Ma, Yangmin
    Dang, Gege
    Qi, Simeng
    Zhang, Xuemei
    Sun, Zhaoyang
    Miao, Xia
    Ma, Siyue
    Zhou, Haojie
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (45)