Bismuth- and Iron-Catalyzed Three-Component Synthesis of α-Amino Acid Derivatives: A Simple and Convenient Route to α-Arylglycines

被引：0
|
作者：
Halli J. [1 ]
Schneider A.E. [1 ]
Beisel T. [1 ]
Kramer P. [1 ]
Shemet A. [1 ]
Manolikakes G. [1 ]
机构：
[1] Department of Organic Chemistry and Chemical Biology, Goethe-University Frankfurt, Max-von-Laue-Straße 7, Frankfurt am Main
来源：
Synthesis (Germany) | 2017年 / 49卷 / 04期
关键词：
amino acids; aza-Friedel-Crafts reaction; bismuth; homogeneous catalysis; iron; multicomponent reactions;
D O I：
10.1055/s-0035-1561499
中图分类号：
学科分类号：
摘要：
Efficient bismuth- and iron-catalyzed three-component syntheses of α-arylglycines have been developed. These methods provide a general, atom-economic route to various N-protected α-arylglycines starting from readily available amides (or carbamates), glyoxalates, and (hetero)arenes with water as the only by-product. Scope and limitations of bismuth- and iron-catalyzed reactions are discussed and compared. In addition, mechanistic investigations as well as initial forays into stereoselective three-component reactions are presented. © Georg Thieme VerlagStuttgart · New York.
引用
收藏
页码：849 / 879
页数：30
相关论文
共 50 条
  • [41] Iron-Catalyzed Ligand-Free Three-Component Coupling Reactions of Aldehydes, Terminal Alkynes, and Amines
    Li, Pinhua
    Zhang, Yicheng
    Wang, Lei
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (09) : 2045 - 2049
  • [42] Three-component Synthesis of Homoallylic Amines Catalyzed by Phosphomolybdic Acid in Water
    Xie Zhengfeng
    Li Guilong
    Zhao Gang
    Wang Jide
    CHINESE JOURNAL OF CHEMISTRY, 2009, 27 (05) : 925 - 929
  • [43] Asymmetric Synthesis of Heterocyclic γ-Amino-Acid and Diamine Derivatives by Three-Component Radical Cascade Reactions
    Zheng, Danqing
    Studer, Armido
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (44) : 15803 - 15807
  • [44] Asymmetric synthesis of quaternary aryl amino acid derivatives via a three-component aryne coupling reaction
    Jones, Elizabeth P.
    Jones, Peter
    White, Andrew J. P.
    Barrett, Anthony G. M.
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2011, 7 : 1570 - 1576
  • [45] Synthesis of unnatural α-amino acid derivatives via a three-component coupling method utilizing an allylpalladium umpolung
    Hopkins, Chad D.
    Malinakova, Helena C.
    SYNTHESIS-STUTTGART, 2007, (22): : 3558 - 3566
  • [46] Development of a copper(II)-catalyzed three-component tandem synthesis of isoindolinone derivatives
    Sun, Leon Xuetong
    Zeng, Tieqiang
    Jiang, Dong
    Dai, Li-Yi
    Li, Chao-Jun
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 2012, 90 (01): : 92 - 99
  • [47] Bismuth(III) chloride-catalyzed one-pot Mannich reaction: three-component synthesis of β-amino carbonyl compounds
    Li, Hua
    Zeng, Hong-yao
    Shao, Hua-wu
    TETRAHEDRON LETTERS, 2009, 50 (49) : 6858 - 6860
  • [48] Photoredox-Catalyzed Carbonyl Alkylative Amination with Diazo Compounds: A Three-Component Reaction for the Construction of ?-Amino Acid Derivatives
    Liu, Geng-Xin
    Liang, Hao-Cheng
    Fu, Xiang
    Tang, Jie
    Hu, Wen-Hao
    Qiu, Huang
    ORGANIC LETTERS, 2022, 24 (27) : 4908 - 4913
  • [49] A Simple and Economic Synthesis of Propargylamines by CuI-Catalyzed Three-Component Coupling Reaction with Succinic Acid as Additive
    Ren, Gerui
    Zhang, Jinli
    Duan, Zheng
    Cui, Mengjun
    Wu, Yangjie
    AUSTRALIAN JOURNAL OF CHEMISTRY, 2009, 62 (01) : 75 - 81
  • [50] Iron-Catalyzed Oxidation of Tertiary Amines: Synthesis of β-1,3-Dicarbonyl Aldehydes by Three-Component C-C Couplings
    Liu, Weiping
    Liu, Jinhua
    Ogawa, Daisuke
    Nishihara, Yasushi
    Guo, Xingwei
    Li, Zhiping
    ORGANIC LETTERS, 2011, 13 (23) : 6272 - 6275
12345