Iron-catalyzed 1,6-addition of aryl Grignard reagents to 2,4-dienoates and -dienamides

被引：66
|
作者：
Fukuhara, K [1 ]
Urabe, H [1 ]
机构：
[1] Tokyo Inst Technol, Dept Biomol Engn, Midori Ku, Yokohama, Kanagawa 2268501, Japan
来源：
TETRAHEDRON LETTERS | 2005年 / 46卷 / 04期
关键词：
Grignard reagents; iron; 1,6-addition; 2,4-dienoate and -dienamide; cis-olefin;
D O I：
10.1016/j.tetlet.2004.11.131
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
1, 6-Addition of aryl Grignard reagents to 2,4-dienoates or -dienamides was nicely catalyzed by iron salt to give 5-aryl-3-enoates or the corresponding amides in a highly regio- and stercoselective manner. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码：603 / 606
页数：4
相关论文
共 50 条
  • [41] Iron-Catalyzed Cross-Coupling of α-Allenyl Esters with Grignard Reagents for the Synthesis of 1,3-Dienes
    Kong, Wei-Jun
    Kessler, Simon N.
    Wu, Haibo
    Backvall, Jan-E
    ORGANIC LETTERS, 2023, : 120 - 124
  • [42] A Practical Procedure for Iron-Catalyzed Cross-Coupling Reactions of Sterically Hindered Aryl-Grignard Reagents with Primary Alkyl Halides
    Sun, Chang-Liang
    Krause, Helga
    Fuerstner, Alois
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (06) : 1281 - 1291
  • [43] Organocatalytic Asymmetric 1,6-Addition/1,4-Addition Sequence to 2,4-Dienals for the Synthesis of Chiral Chromans
    Poulsen, Pernille H.
    Feu, Karla Santos
    Paz, Bruno Matos
    Jensen, Frank
    Jorgensen, Karl Anker
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (28) : 8203 - 8207
  • [44] 1,6-ADDITION OF ORGANOCOPPER REAGENTS TO 3-ALKYNYL-2-CYCLOALKENONES - REGIOSPECIFIC SYNTHESES OF DIENONES AND ALLENES
    CHENG, MY
    HULCE, M
    JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (03): : 964 - 975
  • [45] Preparative and mechanistic studies on copper-mediated 1,6-addition reactions to a 2,4-dienone
    Uerdingen, M
    Krause, N
    TETRAHEDRON, 2000, 56 (18) : 2799 - 2804
  • [46] Regio- and Stereoselective Preparation of β,γ-Unsaturated Carboxylic Acids by One-Pot Sequential Double 1,6-Addition of Grignard Reagents to Methyl Coumalate
    Plevova, Kristina
    Chang, Liang
    Martin, Emmeline
    Llopis, Quentin
    Dechoux, Luc
    Thorimbert, Serge
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (20) : 3293 - 3297
  • [47] Iron-Catalyzed Ring Opening of Cyclopropanols and Their 1,6-Conjugate Addition to p-Quinone Methides
    Mane, Baliram B.
    Waghmode, Suresh B.
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (24): : 17774 - 17781
  • [48] Electronic tuning of chiral diene ligands in iridium-catalyzed asymmetric 1,6-addition of arylboroxines to δ-aryl-α,β,γ,δ-unsaturated ketones
    Nishimura, Takahiro
    Noishiki, Akira
    Hayashi, Tamio
    CHEMICAL COMMUNICATIONS, 2012, 48 (07) : 973 - 975
  • [49] Iron-catalyzed oxidative biaryl cross-couplings via mixed diaryl titanates: significant influence of the order of combining aryl Grignard reagents with titanate
    Liu, Kun Ming
    Wei, Juan
    Duan, Xin Fang
    CHEMICAL COMMUNICATIONS, 2015, 51 (22) : 4655 - 4658
  • [50] Gram-Scale, Cheap, and Eco-Friendly Iron-Catalyzed Cross-Coupling between Alkyl Grignard Reagents and Alkenyl or Aryl Halides
    Cahiez, Gerard
    Lefevre, Guillaume
    Moyeux, Alban
    Guerret, Olivier
    Gayon, Eric
    Guillonneau, Loic
    Lefevre, Nicolas
    Gu, Qinzhuo
    Zhou, Edouard
    ORGANIC LETTERS, 2019, 21 (08) : 2679 - 2683
12345