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] Rhodium-catalyzed enantioselective cyclopropanation of olefins with N-sulfonyl 1,2,3-triazoles
    Chuprakov, Stepan
    Kwok, Sen Wai
    Zhang, Li
    Lercher, Lukas
    Fokin, Valery V.
    Journal of the American Chemical Society, 2009, 131 (50): : 18034 - 18035
  • [42] Chiral Phosphate in Rhodium-Catalyzed Asymmetric [2+2+2] Cycloaddition: Ligand, Counterion, or Both?
    Barbazanges, Marion
    Caytan, Elsa
    Lesage, Denis
    Aubert, Corinne
    Fensterbank, Louis
    Gandon, Vincent
    Ollivier, Cyril
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (25) : 8553 - 8558
  • [43] Solid-phase synthesis of isoindolines via a rhodium-catalyzed [2+2+2] cycloaddition
    Sun, Q
    Zhou, XM
    Islam, K
    Kyle, DJ
    TETRAHEDRON LETTERS, 2001, 42 (37) : 6495 - 6497
  • [44] Rhodium-Catalyzed Asymmetric [2+2+2] Cycloaddition of 1,6-Enynes with Cyclopropylideneacetamides
    Yoshizaki, Soichi
    Nakamura, Yu
    Masutomi, Koji
    Yoshida, Tomoka
    Noguchi, Keiichi
    Shibata, Yu
    Tanaka, Ken
    ORGANIC LETTERS, 2016, 18 (03) : 388 - 391
  • [45] Rhodium-catalyzed enantio- and diastereoselective intramolecular [2+2+2] cycloaddition of unsymmetrical dienynes
    Sagae, Hiromi
    Noguchi, Keiichi
    Hirano, Masao
    Tanaka, Ken
    CHEMICAL COMMUNICATIONS, 2008, (32) : 3804 - 3806
  • [46] Asymmetric synthesis of bicyclic Amidines via rhodium-catalyzed [2+2+2] cycloaddition of Carbodiimides
    Yu, Robert T.
    Rovis, Tomislav
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (11) : 3262 - +
  • [47] Facile Synthesis of Dibenzotetracenedione Derivatives by Rhodium-Catalyzed [2+2+2] Cycloaddition/Spontaneous Aromatization
    Aida, Yukimasa
    Shibata, Yu
    Tanaka, Ken
    CHEMISTRY-AN ASIAN JOURNAL, 2019, 14 (10) : 1823 - 1829
  • [48] Mechanistic Investigation of Cu-Catalyzed Asymmetric Alkynylation of Cyclic N-Sulfonyl Ketimines with Terminal Alkynes
    Zeng, Zhen
    Yan, Fuzhi
    Dai, Moxi
    Yu, Ziwen
    Liu, Fenru
    Zhao, Zhuang
    Bai, Ruopeng
    Lan, Yu
    ORGANOMETALLICS, 2022, 41 (03) : 270 - 277
  • [49] Palladium-catalyzed stereoselective (3+2) cycloaddition of vinylethylene carbonates with cyclic N-sulfonyl ketimines
    Gao, Xing
    Zhu, Dongyu
    Jiang, Feng
    Liao, Jianning
    Wang, Wei
    Wu, Yongjun
    Zheng, Lufei
    Guo, Hongchao
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (22) : 4877 - 4881
  • [50] Rhodium-catalyzed addition of arylboronic acids to N-sulfonyl aldimines
    Ueda, M
    Saito, A
    Miyaura, N
    SYNLETT, 2000, (11) : 1637 - 1639
12345