Catalytic enantioselective passerini three-component reaction

被引:117
|
作者
Wang, Shi-Xin [1 ]
Wang, Mei-Xiang [1 ]
Wang, De-Xian [1 ]
Zhu, Jieping [2 ]
机构
[1] Chinese Acad Sci, Biol Chem Lab, Inst Chem, Natl Lab Mol Sci, Beijing 100080, Peoples R China
[2] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
关键词
aluminum; asymmetric catalysis; isocyanides; multicomponent reactions; salen ligands;
D O I
10.1002/anie.200704315
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Make it enantioselective: The [(salen)-AlIIICl] complex 1 catalyzes the title reaction of an aldehyde, a carboxylic acid, and an isocyanide to afford α-acyloxyamides 2 with good to excellent enantioselectivity. A variety of nonchelating substrates can be used to generate the versatile chiral products. R1 = alkyl; R2 = alkyl, alkenyl, aryl; R3 = alkyl, aryl. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:388 / 391
页数:4
相关论文
共 50 条
  • [41] First enantioselective one-pot, three-component imino Reformatsky reaction
    Cozzi, PG
    Rivalta, E
    PURE AND APPLIED CHEMISTRY, 2006, 78 (02) : 287 - 291
  • [42] Phase behavior and structural determinants of multifuntional tripedal mesogens prepared via the Passerini three-component reaction
    Song, Shuang
    Sahoo, Dipankar
    Kumar, Manoj
    Barkley, Deborah
    Heiney, Paul
    Rudick, Jonathan
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
  • [43] Chiral Bronsted Acid-Catalyzed Enantioselective Three-Component Povarov Reaction
    Liu, Hua
    Dagousset, Guillaume
    Masson, Geraldine
    Retailleau, Pascal
    Zhu, Jieping
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (13) : 4598 - +
  • [44] A catalytic asymmetric three-component 1,4-addition/aldol reaction: Enantioselective synthesis of the spirocyclic system of vannusal A
    Nicolaou, KC
    Tang, WJ
    Dagneau, P
    Faraoni, R
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (25) : 3874 - 3879
  • [45] Sustainable Modification of Carboxymethyl Cellulose by Passerini Three-Component Reaction and Subsequent Adsorption onto Cellulosic Substrates
    Pettignano, Asja
    Daunay, Adelie
    Moreau, Celine
    Cathala, Bernard
    Charlot, Aurelia
    Fleury, Etienne
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2019, 7 (17): : 14685 - 14696
  • [46] Divergent Dendrimer Synthesis via the Passerini Three-Component Reaction and Olefi n Cross-Metathesis
    Kreye, Oliver
    Kugele, Dennis
    Faust, Lorenz
    Meier, Michael A. R.
    MACROMOLECULAR RAPID COMMUNICATIONS, 2014, 35 (03) : 317 - 322
  • [47] Sequence-Regulated Polymers via Combination of Orthogonal Passerini Three-Component Reaction and Thiol-ene Reaction
    Zhang, Jian
    Deng, Xin-Xing
    Du, Fu-Sheng
    Li, Zi-Chen
    SEQUENCE-CONTROLLED POLYMERS: SYNTHESIS, SELF-ASSEMBLY, AND PROPERTIES, 2014, 1170 : 223 - 234
  • [48] Direct catalytic asymmetric three-component Kabachnik-Fields reaction
    Cheng, Xu
    Goddard, Richard
    Buth, Gernot
    List, Benjamin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (27) : 5079 - 5081
  • [49] A simple one-pot, three-component, catalytic, highly enantioselective isoxazolidine synthesis
    Rios, Ramon
    Ibrahem, Ismail
    Vesely, Jan
    Zhao, Gui-Ling
    Cordova, Armando
    TETRAHEDRON LETTERS, 2007, 48 (32) : 5701 - 5705
  • [50] A highly diastereoselective, catalytic three-component assembly reaction for the synthesis of spiropyrrolidinyloxindoles
    Galliford, Chris V.
    Martenson, James S.
    Stern, Charlotte
    Scheidt, Karl A.
    CHEMICAL COMMUNICATIONS, 2007, (06) : 631 - 633