Calcium-Catalyzed Dynamic Multicomponent Reaction

被引:22
|
作者
Gao, Shuang [1 ]
Stopka, Tobias [1 ]
Niggemann, Meike [1 ]
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
关键词
CHEMISTRY; HETEROCYCLES; SOLVOLYSIS;
D O I
10.1021/acs.orglett.5b02593
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reversible formation of covalent bonds enabled by the remarkably high Lewis acidity of our calcium-based catalyst system was used for the development of a new type of multicomponent reaction. Accordingly, a pharmacologically interesting bicyclic amine was amplified from a highly efficient dynamic equilibrium. The product is formed with full diastereoselectivity, and as typical for our calcium-catalyzed reactions, precautions for the exclusion of air and moisture are unnecessary.
引用
收藏
页码:5080 / 5083
页数:4
相关论文
共 50 条
  • [21] Copper-Catalyzed Cascade Multicomponent Reaction of Azides, Alkynes, and Selenium: Synthesis of Ditriazolyl Diselenides
    Sun, Bo-Xun
    Wang, Xu-Nan
    Fan, Tai-Gang
    Hou, Yu-Jian
    Shen, Yun-Tao
    Li, Ya-Min
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (07) : 4528 - 4535
  • [22] Glycine-Catalyzed Efficient Synthesis of Pyranopyrazoles via One-Pot Multicomponent Reaction
    Reddy, M. B. Madhusudana
    Jayashankara, V. P.
    Pasha, M. A.
    SYNTHETIC COMMUNICATIONS, 2010, 40 (19) : 2930 - 2934
  • [23] Synthesis and Microbial Evaluation of Versatile Base Catalyzed Chiral Tetrahydrobenzofuran Derivatives via Multicomponent Reaction
    Kapadiya, Khushal
    Kotadiya, Rohit
    Kavadia, Kishor
    Kothari, Ramesh
    Mehariya, Krunal
    Khunt, Ranjan
    LETTERS IN DRUG DESIGN & DISCOVERY, 2016, 13 (06) : 505 - 513
  • [24] Generation of Sulfonylated Tetrazoles through an Iron-Catalyzed Multicomponent Reaction Involving Sulfur Dioxide
    Zhang, Jun
    Wang, Xuefeng
    Kuang, Yunyan
    Wu, Jie
    ISCIENCE, 2020, 23 (12)
  • [25] A Multicomponent Reaction Towards N-(Cyanomethyl)amides
    Elders, Niels
    Ruijter, Eelco
    de Kanter, Frans J. J.
    Janssen, Elwin
    Lutz, Martin
    Spek, Anthony L.
    Orru, Romano V. A.
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (25) : 6096 - 6099
  • [26] A tunable copper-catalyzed multicomponent reaction towards alkaloid-inspired indole/lactam polycycles
    Mardjan, M. I. D.
    Perie, S.
    Parrain, J. -L.
    Commeiras, L.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (15) : 3304 - 3309
  • [27] Dynamic Multicomponent Hemiaminal Assembly
    You, Lei
    Long, S. Reid
    Lynch, Vincent M.
    Anslyn, Eric V.
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (39) : 11017 - 11023
  • [28] Carbon nanotubes as heterogeneous catalysts for the multicomponent reaction synthesis of heterocycles
    Javahershenas, Ramin
    Soloshonok, Vadim A.
    Klika, Karel D.
    Jervise, Peter J.
    CARBON LETTERS, 2024, : 385 - 385
  • [29] An acid-catalyzed 1,4-addition isocyanide-based multicomponent reaction in neat water
    Lei, Jie
    Li, Yong
    Xu, Jia
    Tang, Dian-Yong
    Shao, Jing-Wei
    Li, Hong-yu
    Chen, Zhong-Zhu
    Xu, Zhi-Gang
    GREEN CHEMISTRY, 2020, 22 (12) : 3716 - 3720
  • [30] Copper(i)-catalyzed multicomponent interrupted click reaction: modular synthesis of triazole sulfides from elemental sulfur
    Sun, Pengfei
    Wang, Weiguo
    Lai, Jilong
    Yan, Huang
    Tung, Chen-Ho
    Xu, Zhenghu
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (08) : 1890 - 1896