Asymmetric Inverse-Electron-Demand 1,3-Dipolar Cycloaddition of C,N-Cyclic Azomethine Imines: An Umpolung Strategy

被引：133
|
作者：
Hashimoto, Takuya [1 ]
Omote, Masato [1 ]
Maruoka, Keiji [1 ]
机构：
[1] Kyoto Univ, Dept Chem, Grad Sch Sci, Sakyo Ku, Kyoto 6068502, Japan
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 15期
关键词：
Bronsted acids; carboxylic acid; cycloadditions; organocatalysis; umpolung; CHIRAL DICARBOXYLIC-ACID; N-BOC IMINES; LEWIS-ACID; ENANTIOSELECTIVE ADDITION; TERMINAL ALKYNES; NITRONES; N; N-DIALKYLHYDRAZONES; N-DIMETHYLHYDRAZONES; CONSTRUCTION; ALDEHYDES;
D O I：
10.1002/anie.201100331
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Oompa loompa: The title reaction has been accomplished with high stereoselectivity by use of an axially chiral dicarboxylic acid (see scheme). Employment of vinylogous aza-enamines as novel dipolarophiles was also implemented to establish a new concept of the inverse-electron-demand umpolung 1,3-dipolar cycloaddition. Bz=benzoyl, EDG=electron-donating group. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：3489 / 3492
页数：4
相关论文
共 50 条
  • [1] Organocatalytic Asymmetric Inverse-Electron-Demand 1,3-Dipolar Cycloaddition of N,N′-Cyclic Azomethine Imines
    Zhu, Ren-Yi
    Wang, Cong-Shuai
    Zheng, Jian
    Shi, Feng
    Tu, Shu-Jiang
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (19) : 9305 - 9312
  • [2] Catalytic Asymmetric Inverse-Electron-Demand 1,3-Dipolar Cycloaddition of C,N-Cyclic Azomethine Imines with Azlactones: Access to Chiral Tricyclic Tetrahydroisoquinolines
    Liu, Xihong
    Wang, Yijie
    Yang, Dongxu
    Zhang, Jinlong
    Liu, Dongsheng
    Su, Wu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (28) : 8100 - 8103
  • [3] Catalytic Enantioselective 1,3-Dipolar Cycloaddition of C,N-Cyclic Azomethine Imines with α,β-Unsaturated Aldehydes
    Hashimoto, Takuya
    Maeda, Yuko
    Omote, Masato
    Nakatsu, Hiroki
    Maruoka, Keiji
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (12) : 4076 - +
  • [4] Enantioselective 1,3-dipolar cycloaddition of methyleneindolinones and N, N′-cyclic azomethine imines
    Hong, Liang
    Kai, Ming
    Wu, Chongyang
    Sun, Wangsheng
    Zhu, Gongming
    Li, Guofeng
    Yao, Xiaojun
    Wang, Rui
    CHEMICAL COMMUNICATIONS, 2013, 49 (60) : 6713 - 6715
  • [5] Amine-Catalyzed Enantioselective 1,3-Dipolar Cycloadditions of Aldehydes to C, N-Cyclic Azomethine Imines
    Li, Wenjun
    Jia, Qianfa
    Du, Zhiyun
    Zhang, Kun
    Wang, Jian
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (16) : 4559 - 4562
  • [6] Copper-catalyzed 1,3-dipolar cycloaddition of methyleneindolinones and N,N′-cyclic azomethine imines
    Zhang, Di
    Zhang, Da-Ming
    Xu, Guang-Yang
    Sun, Jiang-Tao
    CHINESE CHEMICAL LETTERS, 2015, 26 (03) : 301 - 303
  • [7] 1,3-Dipolar cycloaddition of isatinN,N′-cyclic azomethine imines with α,β-unsaturated aldehydes catalyzed by DBU in water
    Wang, Zhan-Yong
    Yang, Ting
    Chen, Rongxiang
    Ma, Xueji
    Liu, Huan
    Wang, Kai-Kai
    RSC ADVANCES, 2020, 10 (41) : 24288 - 24292
  • [8] Nickel(II)-Catalyzed Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Imines with Alkylidene Malonates
    Li, Jiangting
    Lian, Xiangjin
    Liu, Xiaohua
    Lin, Lili
    Feng, Xiaoming
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (16) : 5134 - 5140
  • [9] Asymmetric Organocatalytic 1,3-Dipolar Cycloaddition of Azomethine Ylides with β-Substituted Cyclic Enones
    Zhong, Han
    Zhang, Xiao-Yi
    Yao, Yong-Mou
    Chen, Wen-Ming
    Wang, Wei
    Tian, Xu
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (14) : 9721 - 9732
  • [10] Synthesis of Spirocyclic Amines by 1,3-Dipolar Cycloaddition of Azomethine Ylides and Azomethine Imines
    Choi, Anthony
    Castle, Jemma
    Saruengkhanphasit, Rungroj
    Coldham, Iain
    SYNTHESIS-STUTTGART, 2020, 52 (08): : 1273 - 1278
12345