Palladium-Catalyzed Ring Opening of Aminocyclopropyl Ugi Adducts

被引:12
|
作者
Dos Santos, Aurelie [1 ]
El Kaim, Laurent [1 ]
Grimaud, Laurence [1 ]
Ramozzi, Romain [1 ]
机构
[1] Ecole Natl Super Tech Avancees, UMR 7652, Lab DCSO ENSTA Polytech CNRS, F-75739 Paris 15, France
关键词
aminocyclopropanes; ring opening; palladium; Ugi; Ugi-Smiles; ORGANIC-SYNTHESIS; MULTICOMPONENT REACTIONS; 3+2 CYCLOADDITIONS; CYCLOPROPANES; DERIVATIVES; CHEMISTRY; METHYLENECYCLOPROPANES; SILOXYCYCLOPROPANES; REARRANGEMENTS; CYCLIZATION;
D O I
10.1055/s-0031-1290312
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The ring opening of aminocyclopropanes triggered by activation with an intramolecular arylpalladium(II) iodide complex is an interesting strategy for the synthesis of nitrogen heterocycles and a valuable Ugi postcondensation-type transformation. Six- and seven-membered-ring cyclic enamines may be obtained.
引用
收藏
页码:438 / 442
页数:5
相关论文
共 50 条
  • [1] Palladium-catalyzed enantioselective alkylative ring opening
    Lautens, M
    Renaud, JL
    Hiebert, S
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (08) : 1804 - 1805
  • [2] Scope of palladium-catalyzed alkylative ring opening
    Lautens, M
    Hiebert, S
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (05) : 1437 - 1447
  • [3] Palladium-Catalyzed Ring-Opening Alkynylation of Cyclopropenones
    Matsuda, Takanori
    Sakurai, Yusuke
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (20) : 4219 - 4222
  • [4] Ring opening in the palladium-catalyzed hydrocarbonation of methylenecyclopropanes with pronucleophiles
    Tsukada, N
    Shibuya, A
    Nakamura, I
    Yamamoto, Y
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (34) : 8123 - 8124
  • [5] Synthesis of Cyclitols via Cyclopropanation/Palladium-Catalyzed Ring Opening
    Shan, Mingde
    O'Doherty, George A.
    SYNTHESIS-STUTTGART, 2008, 19 (19): : 3171 - 3179
  • [6] Palladium-Catalyzed Ring-Opening Diarylation of Cyclobutanols for the Synthesis of Acylindanes
    Yan, Wen-Jing
    Tu, Hai-Yong
    Liao, Zhiyong
    Shen, Xiao-Qin
    Zhang, Xing-Guo
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (13) : 2147 - 2151
  • [7] Palladium-Catalyzed Ring-Opening Reaction of Cyclopropenones with Vinyl Epoxides
    Lu, Li-Guo
    Chen, Jun-Hua
    Huang, Xiao-Bo
    Liu, Miao-Chang
    Zhou, Yun-Bing
    Wu, Hua-Yue
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (24): : 16851 - 16859
  • [8] Mechanistic studies of the palladium-catalyzed ring opening of oxabicyclic alkenes with dialkylzinc
    Lautens, M
    Hiebert, S
    Renaud, JL
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (28) : 6834 - 6839
  • [9] Palladium-catalyzed enantioselective ring opening of oxabicyclic alkenes with organozinc halides
    Li, M
    Yan, XX
    Hong, W
    Zhu, XZ
    Cao, BX
    Sun, J
    Hou, XL
    ORGANIC LETTERS, 2004, 6 (16) : 2833 - 2835
  • [10] Palladium-Catalyzed Ring-Opening Coupling of Cyclobutenols with Aryl Halides
    Matsuda, Takanori
    Matsumoto, Takeshi
    Murakami, Akira
    SYNLETT, 2018, 29 (06) : 754 - 758