Copper-catalyzed asymmetric Michael reactions with a-amino acid amides: Synthesis of an optically active piperidine derivative

被引:0
|
作者
Christoffers, J [1 ]
Scharl, H [1 ]
机构
[1] Univ Stuttgart, Inst Organ Chem, D-70569 Stuttgart, Germany
关键词
asymmetric synthesis; catalysis; C-C coupling; copper; Michael additions;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Quaternary stereocenters are obtained at room temperature in copper-catalyzed asymmetric Michael reactions with alpha-amino acid amides as chiral auxiliaries. L-Valine diethylamide was applied as a chiral auxiliary, and an optically active piperidine derivative was prepared with 97% ee. The optical purity of the product was established by GLC after cyclization to a hexahydroisoquinolonecarboxylate. ((C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).
引用
收藏
页码:1505 / 1508
页数:4
相关论文
共 50 条
  • [1] A novel L-neopentylglycine derivative as auxiliary for copper-catalyzed asymmetric Michael reactions
    Christoffers, J
    Schuster, K
    CHIRALITY, 2003, 15 (09) : 777 - 782
  • [2] Lewis Acid Enabled Copper-Catalyzed Asymmetric Synthesis of Chiral β-Substituted Amides
    Rodriguez-Fernandez, Mamen
    Yan, Xingchen
    Collados, Juan F.
    White, Paul B.
    Harutyunyan, Syuzanna R.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (40) : 14224 - 14231
  • [3] Synthesis of a-Amino Acid Amides: Ruthenium-Catalyzed Amination of a-Hydroxy Amides
    Zhang, Min
    Imm, Sebastian
    Baehn, Sebastian
    Neumann, Helfried
    Beller, Matthias
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (47) : 11197 - 11201
  • [4] Asymmetric Synthesis of γ-Amino Alcohols by Copper-Catalyzed Hydroamination
    Ichikawa, Saki
    Buchwald, Stephen L.
    ORGANIC LETTERS, 2019, 21 (21) : 8736 - 8739
  • [5] Copper-Catalyzed Asymmetric Kinugasa/Michael Addition Cascade Reactions for the Synthesis of Chiral Spiro β-Lactams
    Ao, Yunlin
    Ma, Haowen
    Gan, Binghan
    Wang, Wenjing
    Zhang, Jiehao
    Zhou, Wei
    Zhang, Xiaoqi
    Cai, Qian
    ORGANIC LETTERS, 2024, 26 (22) : 4761 - 4766
  • [6] Asymmetric Synthesis of Spirocyclic-Lactams through Copper-Catalyzed Kinugasa/Michael Domino Reactions
    Shu, Tao
    Zhao, Long
    Li, Sun
    Chen, Xiang-Yu
    von Essen, Carolina
    Rissanen, Kari
    Enders, Dieter
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (34) : 10985 - 10988
  • [7] COPPER-CATALYZED REACTIONS FOR THE SYNTHESIS OF BIOLOGICALLY ACTIVE HETEROCYCLES
    Beifuss, Uwe
    MEDICINAL CHEMISTRY RESEARCH, 2010, 19 : S9 - S10
  • [8] Copper-Catalyzed Asymmetric Aminocyanation of Arylcyclopropanes for Synthesis of γ-Amino Nitriles
    Yang, Shengbiao
    Wang, Lihong
    Zhang, Hongwei
    Liu, Chunyang
    Zhang, Linli
    Wang, Xiaomin
    Zhang, Ge
    Li, Yan
    Zhang, Qian
    ACS CATALYSIS, 2019, 9 (01) : 716 - 721
  • [9] Formation of quaternary stereocenters by copper-catalyzed Michael reactions with L-valine amides as auxiliaries
    Christoffers, J
    CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (20) : 4862 - 4867
  • [10] Copper-Catalyzed Asymmetric Hydroamination: A Unified Strategy for the Synthesis of Chiral β-Amino Acid and Its Derivatives
    Zhang, Ge
    Liang, Yujie
    Qin, Tao
    Xiong, Tao
    Liu, Shuyu
    Guan, Wei
    Zhang, Qian
    CCS CHEMISTRY, 2021, 3 (07): : 1737 - 1745