Rhodium-catalyzed [2+2+2] cycloaddition reactions of terminal alkynes with N-sulfonyl ketimines

被引：5
|
作者：
Zhang, Wei [1 ]
Zhang, Qian-Ru [1 ]
Dong, Lin [1 ]
机构：
[1] Sichuan Univ, Key Lab Drug Targeting & Drug Delivery Syst, Educ Minist, West China Sch Pharm, Chengdu 610041, Peoples R China
来源：
TETRAHEDRON LETTERS | 2015年 / 56卷 / 03期
关键词：
1,2-Dihydropyridines; Rhodium; Terminal alkynes; 2+2+2] cycloaddition; N-Sulfonyl ketimines; STEREOSELECTIVE-SYNTHESIS; AZA-NICKELACYCLE; IMINES; PYRIDINES; 1,2-DIHYDROPYRIDINES; CYCLIZATION; CHEMISTRY;
D O I：
10.1016/j.tetlet.2014.11.122
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple approach for the direct synthesis of 1,2-dihydropyridines was developed involving a one-step rhodium-catalyzed [2+2+2] cycloaddition between N-sulfonyl ketimines and two terminal alkynes. Mechanistic studies suggested a stepwise reaction of an imine and alkyne with rhodium(III), followed by the insertion of a second alkyne. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：546 / 548
页数：3
相关论文
共 50 条
  • [41] Highly enantioselective synthesis of N,N-dialkylbenzamides with aryl-carbonyl axial chirality by rhodium-catalyzed [2+2+2] cycloaddition
    Suda, Takeshi
    Noguchi, Keiichi
    Hirano, Masao
    Tanaka, Ken
    CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (22) : 6593 - 6596
  • [42] Synthesis of Single and Double Dibenzohelicenes by Rhodium-Catalyzed Intramolecular [2+2+2] and [2+1+2+1] Cycloaddition
    Yamano, Ryota
    Shibata, Yu
    Tanaka, Ken
    CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (24) : 6364 - +
  • [43] Rhodium-Catalyzed [2+2+2] Cycloaddition Reactions of Linear Allene-Ene-Ynes to afford Fused Tricyclic Scaffolds: Insights into the Mechanism
    Cassu, Daniel
    Parella, Teodor
    Sola, Miquel
    Pla-Quintana, Anna
    Roglans, Anna
    CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (59) : 14889 - 14899
  • [44] Enantioselective Rhodium-Catalyzed [2+2+2] Cycloadditions of Terminal Alkynes and Alkenyl Isocyanates: Mechanistic Insights Lead to a Unified Model that Rationalizes Product Selectivity
    Dalton, Derek M.
    Oberg, Kevin M.
    Yu, Robert T.
    Lee, Ernest E.
    Perreault, Stephane
    Oinen, Mark Emil
    Pease, Melissa L.
    Malik, Guillaume
    Rovis, Tomislav
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (43) : 15717 - 15728
  • [45] Aerobic Oxidative C-H Olefination of Cyclic N-Sulfonyl Ketimines Catalyzed by a Rhodium Catalyst
    Wang, Nan-Jin
    Mei, Shu-Tao
    Shuai, Li
    Yuan, Yi
    Wei, Ye
    ORGANIC LETTERS, 2014, 16 (11) : 3040 - 3043
  • [46] Catalytic activity of a large Rhodium metallaborane towards the [2+2+2] cycloaddition of alkynes
    Ma, Pei
    Spencer, James T.
    INORGANICA CHIMICA ACTA, 2018, 482 : 67 - 69
  • [47] Total Synthesis of Indolizidine Alkaloid (-)-209D: Overriding Substrate Bias in the Asymmetric Rhodium-Catalyzed [2+2+2] Cycloaddition
    Yu, Robert T.
    Lee, Ernest E.
    Malik, Guillaume
    Rovis, Tomislav
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (13) : 2379 - 2382
  • [48] Rhodium-Catalyzed [2+2+2] Cycloaddition-Aromatization of 1,6-Diynes with Cyclic Enol Ethers at Room Temperature
    Aida, Yukimasa
    Tooriyama, Shino
    Kimura, Yuki
    Hara, Hiromi
    Shibata, Yu
    Tanaka, Ken
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (01) : 132 - 138
  • [49] Ni-catalyzed enantioselective [2+2+2] cycloaddition of malononitriles with alkynes
    Cai, Jinhui
    Bai, Li-Gang
    Zhang, Yiliang
    Wang, Zhen-Kai
    Yao, Fei
    Peng, Jin-Huang
    Yan, Wei
    Wang, Yan
    Zheng, Chao
    Liu, Wen-Bo
    CHEM, 2021, 7 (03): : 799 - 811
  • [50] Nickel-catalyzed [2+2+2] cycloaddition of two alkynes and an imine
    Ogoshi, Sensuke
    Ikeda, Haruo
    Kurosawa, Hideo
    PURE AND APPLIED CHEMISTRY, 2008, 80 (05) : 1115 - 1125
12345