Amine-Catalyzed Enantioselective 1,3-Dipolar Cycloadditions of Aldehydes to C, N-Cyclic Azomethine Imines

被引：44
|
作者：
Li, Wenjun [1 ,2 ]
Jia, Qianfa [2 ]
Du, Zhiyun [2 ]
Zhang, Kun [2 ]
Wang, Jian [1 ,2 ]
机构：
[1] Guangdong Univ Technol, Allan H Conney Lab Anticanc Res, Guangzhou 510006, Guangdong, Peoples R China
[2] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2014年 / 20卷 / 16期
关键词：
asymmetric synthesis; cycloadditions; enamines; heterocycles; tetrahydroisoquinoline; PICTET-SPENGLER CONDENSATION; CHIRAL IMINIUM IONS; BETA-PHENYLETHYLAMINES; RECENT PROGRESS; ISOQUINOLINE; FORMAMIDINES; HYDROGENATION; LATRUNCULIA; DERIVATIVES; ALKALOIDS;
D O I：
10.1002/chem.201400333
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Amine-catalyzed enantioselective 1,3-dipolar cycloadditions of aldehydes to C,N-cyclic azomethine imines were developed. The reactions between diversely substituted C,N-cyclic azomethine imines and aldehydes proceeded smoothly in the presence of chiral prolinol silyl ether catalyst and gave the C-1-substituted tetrahydroisoquinolines in a highly stereoselective manner. These tetrahydroisoquinolines could be efficiently transformed to several other useful polycyclic frameworks.
引用
收藏
页码：4559 / 4562
页数：4
相关论文
共 50 条
  • [1] 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 - +
  • [2] Control of the Dual Reactivity (Iminium-Dienamine) of β-Arylmethyl α,β-Unsaturated Aldehydes in Organocatalytic 1,3-Dipolar Cycloadditions with N-Benzoyl C,N-Cyclic Azomethine Imines
    Izquierdo, Cristina
    Esteban, Francisco
    Parra, Alejandro
    Alfaro, Ricardo
    Aleman, Jose
    Fraile, Alberto
    Garcia Ruano, Jose Luis
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (21) : 10417 - 10433
  • [3] 1,3-Dipolar cycloadditions of azomethine imines
    Najera, Carmen
    Sansano, Jose M.
    Yus, Miguel
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (32) : 8596 - 8636
  • [4] 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
  • [5] 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
  • [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] Asymmetric Inverse-Electron-Demand 1,3-Dipolar Cycloaddition of C,N-Cyclic Azomethine Imines: An Umpolung Strategy
    Hashimoto, Takuya
    Omote, Masato
    Maruoka, Keiji
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (15) : 3489 - 3492
  • [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] Cross 1,3-dipolar cycloadditions of C, N- cyclic azomethine imines with an N- benzyl azomethine ylide: facile access to fused tricyclic 1,2,4-hexahydrotriazines
    Wang, Kai-Kai
    Li, Yan-Li
    Wang, Zhan-Yong
    Hu, Meng-Wei
    Qiu, Ting-Ting
    Zhu, Bao-Ku
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (02) : 244 - 247
  • [10] Catalyst-free and atom-economical 1,3-dipolar cycloaddition of C,N-cyclic azomethine imines: Facile synthesis of isoquinoline-fused spirocycles
    Li, Lesong
    Liu, Tao
    Zhang, Xiaoli
    Hou, Xiaohan
    Dong, Hao
    Li, Xiaoyang
    Ren, Weiwu
    Wang, Yang
    GREEN SYNTHESIS AND CATALYSIS, 2022, 3 (01): : 69 - 78
12345