Bronsted Acid Catalyzed Enantioselective Three-Component Reaction Involving the α Addition of Isocyanides to Imines

被引:149
|
作者
Yue, Tao [1 ,2 ]
Wang, Mei-Xiang [1 ,2 ]
Wang, De-Xian [1 ,2 ]
Masson, Geraldine [3 ]
Zhu, Jieping [3 ]
机构
[1] Chinese Acad Sci, Inst Chem, Biol Chem Lab, Natl Nat Lab Mol Sci, Beijing 100190, Peoples R China
[2] Tsinghua Univ, Dept Chem, Minist Educ, Key Lab Bioorgan Phosphrous Chem & Chem Biol, Beijing 100084, Peoples R China
[3] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
基金
美国国家科学基金会;
关键词
asymmetric synthesis; heterocycles; multicomponent reactions; organocatalysis; Ugi reaction; TERMINAL CARBOXYLIC-ACID; FRIEDEL-CRAFTS REACTION; MULTICOMPONENT REACTIONS; AMINO-ACID; ASYMMETRIC-SYNTHESIS; BIARYL ETHER; RAPID ACCESS; CONSTRUCTION; 5-AMINOOXAZOLE; MACROCYCLES;
D O I
10.1002/anie.200902385
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
All three together now: Three-component reactions of aldehydes, anilines, and α-isocyanoacetamides in the presence of a catalytic amount of chiral phosphoric acid afforded the 5-(1-aminoalkyl)-5-aminooxazole 1 in excellent yields and moderate to good enantiomeric excess (see scheme). © 2009 Wiley-VCH Verlag GmbH & Co. KCaA.
引用
收藏
页码:6717 / 6721
页数:5
相关论文
共 50 条
  • [1] Chiral Bronsted Acid-Catalyzed Enantioselective Three-Component Povarov Reaction
    Liu, Hua
    Dagousset, Guillaume
    Masson, Geraldine
    Retailleau, Pascal
    Zhu, Jieping
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (13) : 4598 - +
  • [2] Enantioselective Bronsted acid catalyzed addition reactions of methyleneaminopyrrolidine to imines
    Dixon, DJ
    Tillman, AL
    [J]. SYNLETT, 2005, (17) : 2635 - 2638
  • [3] Enantioselective three-component Ugi reaction catalyzed by chiral phosphoric acid
    Zhang, Jian
    Wang, Yi-Yan
    Sun, He
    Li, Shao-Yu
    Xiang, Shao-Hua
    Tan, Bin
    [J]. SCIENCE CHINA-CHEMISTRY, 2020, 63 (01) : 47 - 54
  • [4] Enantioselective three-component Ugi reaction catalyzed by chiral phosphoric acid
    Jian Zhang
    Yi-Yan Wang
    He Sun
    Shao-Yu Li
    Shao-Hua Xiang
    Bin Tan
    [J]. Science China Chemistry, 2020, 63 : 47 - 54
  • [5] Enantioselective three-component Ugi reaction catalyzed by chiral phosphoric acid
    Jian Zhang
    YiYan Wang
    He Sun
    ShaoYu Li
    ShaoHua Xiang
    Bin Tan
    [J]. Science China(Chemistry)., 2020, 63 (01) - 54
  • [6] Enantioselective three-component Ugi reaction catalyzed by chiral phosphoric acid
    Jian Zhang
    Yi-Yan Wang
    He Sun
    Shao-Yu Li
    Shao-Hua Xiang
    Bin Tan
    [J]. Science China Chemistry, 2020, (01) : 47 - 54
  • [7] A Three-Component Enantioselective Cyclization Reaction Catalyzed by an Unnatural Amino Acid Derivative
    de Gracia Retamosa, Maria
    Ruiz-Olalla, Andrea
    Bello, Tamara
    de Cozar, Abel
    Cossio, Fernando P.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (03) : 668 - 672
  • [8] Enantioselective Assembly of α, β-Diamine Acid Derivatives via Three-Component Reaction of α-H Diazoacetates with Sulfonamides and Imines
    Sha, Hongkai
    Xie, Xiongda
    Zhang, Dan
    Hu, Wenhao
    Kang, Zhenghui
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (24) : 4609 - 4615
  • [9] Enantioselective Palladium(II) Phosphate Catalyzed Three-Component Reactions of Pyrrole, Diazoesters, and Imines
    Zhang, Dan
    Qiu, Huang
    Jiang, Liqin
    Lv, Fengping
    Ma, Chaoqun
    Hu, Wenhao
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (50) : 13356 - 13360
  • [10] Bronsted Acid-Catalyzed Three-Component Reaction of Anilines, α-Oxoaldehydes, and α-Angelicalactone for the Synthesis of Complex Pyrrolidones
    Huo, Congde
    Yuan, Yong
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (24): : 12704 - 12710