Revisited Mechanistic Implications of the Joullie-Ugi Three-Component Reaction

被引:36
|
作者
Katsuyama, Akira [1 ]
Matsuda, Akira [1 ,2 ]
Ichikawa, Satoshi [1 ,2 ]
机构
[1] Hokkaido Univ, Fac Pharmaceut Sci, Kita Ku, Kita 12,Nishi 6, Sapporo, Hokkaido 0600812, Japan
[2] Hokkaido Univ, Fac Pharmaceut Sci, Ctr Res & Educ Drug Discovery, Kita Ku, Kita 12,Nishi 6, Sapporo, Hokkaido 0600812, Japan
关键词
D O I
10.1021/acs.orglett.6b00827
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The effect of the solvent on the diastereoselectivity of the Joullie-Ugi three-component reaction (JU-3CR) using an alpha-substituted five-membered cyclic imine is revisited. The cis and trans isomers were generated in toluene and HFIP, respectively. Hammett analysis of the JU-3CR suggests the presence of two reaction mechanisms.
引用
收藏
页码:2552 / 2555
页数:4
相关论文
共 50 条
  • [1] Total Synthesis of Plusbacin A3 Using a Diastereoseletive Joullie-Ugi Three Component Reaction
    Katsuyama, Akira
    Ichikawa, Satoshi
    [J]. JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2019, 77 (07) : 663 - 672
  • [2] Glyco- and peptidomimetics from three-component Joullie-Ugi coupling show selective antiviral activity
    Chapman, TM
    Davies, IG
    Gu, B
    Block, TM
    Scopes, DIC
    Hay, PA
    Courtney, SM
    McNeill, LA
    Schofield, CJ
    Davis, BG
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (02) : 506 - 507
  • [3] Total Synthesis of Plusbacin A3 and Its Dideoxy Derivative Using a Solvent-Dependent Diastereodivergent Joullie-Ugi Three-Component Reaction
    Katsuyama, Akira
    Yakushiji, Fumika
    Ichikawa, Satoshi
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (13): : 7085 - 7101
  • [4] N-Isocyanodialkylamines generated in situ for the Joullie-Ugi reaction with indolenines
    Golubev, Pavel
    Krasavin, Mikhail
    [J]. TETRAHEDRON LETTERS, 2018, 59 (39) : 3532 - 3536
  • [5] Catalytic three-component Ugi reaction
    Pan, Subhas Chandra
    List, Benjamin
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (19) : 3622 - 3625
  • [6] Catalytic asymmetric three-component Ugi reaction
    Zhao, Wenjun
    Huang, Li
    Guan, Yong
    Wulff, William D.
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 246
  • [7] The Ugi three-component reaction and its variants
    Cesar Flores-Reyes, Julio
    Islas-Jacome, Alejandro
    Gonzalez-Zamora, Eduardo
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (19) : 5460 - 5515
  • [8] Lewis Acid-Catalyzed Diastereoselective Synthesis of Multisubstituted N-Acylaziridine-2-carboxamides from 2H-Azirines via Joullie-Ugi Three-Component Reaction
    Angyal, Aniko
    Demjen, Andras
    Weber, Edit
    Kovacs, Anita K.
    Wolfling, Janos
    Puskas, Laszlo G.
    Kanizsai, Ivan
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (07): : 3570 - 3581
  • [9] DFT Studies on the Stereoselective Three-Component Ugi Reaction
    Sharifzadeh, Elaheh Sadat
    Shiraz, Nader Zabarjad
    [J]. ORBITAL-THE ELECTRONIC JOURNAL OF CHEMISTRY, 2019, 11 (01): : 18 - 24
  • [10] Indoline-Based Constrained Peptidomimetic Motifs Obtained via the Joullie-Ugi Reaction of Indolenines
    Golubev, Pavel
    Bakulina, Olga
    Dar'in, Dmitry
    Krasavin, Mikhail
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (23) : 3969 - 3976