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
  • [41] Novel spirocyclic systems via multicomponent aza-Diels-Alder reaction
    Llona-Minguez, Sabin
    Throup, Adam
    Steiner, Emilie
    Lightowler, Molly
    Van der Haegen, Sandra
    Homan, Evert
    Eriksson, Lars
    Stenmark, Pal
    Jenmalm-Jensen, Annika
    Helleday, Thomas
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (37) : 7758 - 7764
  • [42] A Dynamic Multicomponent Approach for One-Pot Synthesis of 3-Thioisoindolinones
    Sakulsombat, Morakot
    Angelin, Marcus
    Caraballo, Remi
    Ramstrom, Olof
    ISRAEL JOURNAL OF CHEMISTRY, 2013, 53 (1-2) : 127 - 132
  • [43] Unusual reactivity of 1-aminoanthraquinone in copper catalyzed multicomponent reaction with isatins and aryl alkynes: synthesis and photophysical properties of regioisomeric fluorescent 3-spiroheterocyclic 2-oxindoles
    Periyaraja, Somasundharam
    Shanmugam, Ponnusamy
    Mandal, Asit Baran
    Kumar, Thiyagarajan Senthil
    Ramamurthy, Perumal
    TETRAHEDRON, 2013, 69 (14) : 2891 - 2899
  • [44] New Heterocyclic Inputs for the Povarov Multicomponent Reaction
    Vicente-Garcia, Esther
    Ramon, Rosario
    Lavilla, Rodolfo
    SYNTHESIS-STUTTGART, 2011, (14): : 2237 - 2246
  • [45] Finding Reaction Pathways for Multicomponent Reactions: The Passerini Reaction is a Four-Component Reaction
    Maeda, Satoshi
    Komagawa, Shinsuke
    Uchiyama, Masanobu
    Morokuma, Keiji
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (03) : 644 - 649
  • [46] Multicomponent Combinatorial Polymerization via the Biginelli Reaction
    Xue, Haodong
    Zhao, Yuan
    Wu, Haibo
    Wang, Zilin
    Yang, Bin
    Wei, Yen
    Wang, Zhiming
    Tao, Lei
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (28) : 8690 - 8693
  • [47] Still Relevant Today: The Asinger Multicomponent Reaction
    Griboura, Nefeli
    Gatzonas, Konstantinos
    Neochoritis, Constantinos G.
    CHEMMEDCHEM, 2021, 16 (13) : 1997 - 2020
  • [48] Palladium-Catalyzed Carbonylative Multicomponent Synthesis of Functionalized Benzimidazothiazoles
    Veltri, Lucia
    Grasso, Giuseppe
    Rizzi, Rosanna
    Mancuso, Raffaella
    Gabriele, Bartolo
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (04) : 560 - 567
  • [49] Ag-catalyzed Multicomponent Synthesis of Heterocyclic Compounds: A Review
    Nia, Roghayeh Hossein
    Mamaghani, Manouchehr
    Tavakoli, Fatemeh
    CURRENT ORGANIC SYNTHESIS, 2022, 19 (04) : 484 - 506
  • [50] Photoinitiated multicomponent cascade reaction of N-heteroarenes with unactivated alkenes and trimethylsilyl azide
    Shen, Jiabin
    He, Lei
    Liang, Chenfeng
    Ouyang, Yani
    Yue, Xiaoguang
    Wu, Haifeng
    Xu, Jun
    Liu, Xiaogang
    Zhu, Qing
    Zhang, Pengfei
    MOLECULAR CATALYSIS, 2022, 524