Highly Diastereo- and Enantioselective Mannich Reactions of Synthetically Flexible Ketimines with Secondary Amine Organocatalysts

被引:74
|
作者
Kano, Taichi [1 ]
Song, Sunhwa [1 ]
Kubota, Yasushi [2 ]
Maruoka, Keiji [1 ]
机构
[1] Kyoto Univ, Dept Chem, Grad Sch Sci, Sakyo Ku, Kyoto 6068502, Japan
[2] Nippon Soda Co Ltd, Odawara, Kanagawa 2500280, Japan
关键词
aldehydes; asymmetric catalysis; ketimines; Mannich reaction; organocatalysis; QUATERNARY CARBON CENTER; ALPHA-AMINO; ASYMMETRIC-SYNTHESIS; EFFICIENT ORGANOCATALYST; C-C; ACID; ALDEHYDES; SULFONAMIDE; KETONES; AMINOMETHYLATION;
D O I
10.1002/anie.201107375
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
引用
收藏
页码:1191 / 1194
页数:4
相关论文
共 50 条
  • [41] Ag-Catalyzed Diastereo- and Enantioselective Vinylogous Mannich Reactions of α-Ketoimine Esters. Development of a Method and Investigation of its Mechanism
    Wieland, Laura C.
    Vieira, Erika M.
    Snapper, Marc L.
    Hoveyda, Amir H.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (02) : 570 - 576
  • [42] Ag-catalyzed diastereo- and enantioselective vinylogous mannich reactions of α-ketoimine esters. Development of a method and investigation of its mechanism
    Wieland, Laura C.
    Vieira, Erika M.
    Snapper, Marc L.
    Hoveyda, Amir H.
    Journal of the American Chemical Society, 2009, 131 (02): : 570 - 576
  • [43] Diastereo- and Enantioselective Reductive Mannich-type Reaction of α,β-Unsaturated Carboxylic Acids to Ketimines: A Direct Entry to Unprotected β2,3,3-Amino Acids
    Suzuki, Hirotsugu
    Kondo, Sora
    Yamada, Koichiro
    Matsuda, Takanori
    CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (04)
  • [44] Highly Enantioselective Three-Component Direct Mannich Reactions of Unfunctionalized Ketones Catalyzed by Bifunctional Organocatalysts
    Guo, Qunsheng
    Zhao, John Cong-Gui
    ORGANIC LETTERS, 2013, 15 (03) : 508 - 511
  • [45] Diastereo- and Enantioselective Access to Stereotriads through a Flexible Coupling of Substituted Aldehydes and Alkenes
    Li, Jing
    Preinfalk, Alexander
    Maulide, Nuno
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (18) : 5887 - 5890
  • [46] Highly diastereo- and enantioselective one-pot Michael-Aldol reactions of α,β-unsaturated aldehydes with imidazole derivatives
    Li, Wenjun
    Li, Xin
    Wu, Wenbin
    Liang, Xinmiao
    Ye, Jinxing
    CHEMICAL COMMUNICATIONS, 2011, 47 (29) : 8325 - 8327
  • [47] Highly Diastereo- and Enantioselective Cascade Synthesis of Bicyclic Lactams in One-Pot
    Jiang, Yan
    Deiana, Luca
    Alimohammadzadeh, Rana
    Liu, Leifeng
    Sun, Junliang
    Cordova, Armando
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (09) : 1158 - 1164
  • [48] Diastereo- and Enantioselective Catalytic Vinylogous Mukaiyama-Mannich Reactions of Pyrrole-Based Silyl Dienolates with Alkyl-Substituted Aldehydes
    Ranieri, Beatrice
    Curti, Claudio
    Battistini, Lucia
    Sartori, Andrea
    Pinna, Luigi
    Casiraghi, Giovanni
    Zanardi, Franca
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (24): : 10291 - 10298
  • [49] A Highly Diastereo- and Enantioselective Synthesis of Tetrahydroquinolines: Quaternary Stereogenic Center Inversion and Functionalization
    Luo, Chaosheng
    Huang, Yong
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (22) : 8193 - 8196
  • [50] Highly diastereo- and enantioselective synthesis of protected anti-1,3-diols
    Enders, D
    Hundertmark, T
    Lampe, C
    Jegelka, U
    Scharfbillig, I
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1998, 1998 (12) : 2839 - 2849