Diastereo- and Enantioselective Synthesis of α,γ-Diaminobutyric Acid Derivatives via Cu-Catalyzed Asymmetric Michael Reaction

被引:49
|
作者
Li, Qing [1 ]
Ding, Chang-Hua [1 ]
Hou, Xue-Long [1 ]
Dai, Li-Xin [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
ALPHA-AMINO-ACIDS; CHIRAL CALCIUM COMPLEXES; PHASE-TRANSFER CATALYSIS; PI-ACCEPTOR LIGANDS; AZOMETHINE YLIDES; 1,3-DIPOLAR CYCLOADDITION; CONJUGATE ADDITIONS; GLYCINE DERIVATIVES; NITROALKENES; HYDROFORMYLATION;
D O I
10.1021/ol100060t
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first highly diastereo- and enantioselective catalytic asymmetric Michael addition of glycine derivatives to nitroalkenes have been developed. The enantioselectivity of ortho-substituted products can be significantly improved by using a new 1,2-P,N-ferrocene ligand L5. The alpha,gamma-diaminoacid derivative was obtained without the loss of optical activity from the adduct.
引用
收藏
页码:1080 / 1083
页数:4
相关论文
共 50 条
  • [41] Diastereo- and Enantioselective Synthesis of Spiro-Pyrrolidine-Pyrazolones by Squaramide-Catalyzed Cascade Aza-Michael/Michael Reactions
    Li, Jun-Hua
    Wen, Hongliang
    Liu, Lei
    Du, Da-Ming
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (14) : 2492 - 2499
  • [44] Cr-Catalyzed Diastereo- and Enantioselective Synthesis of β-Hydroxy Sulfides and Selenides
    Xia, Xiaowen
    Wang, Zhaobin
    ACS CATALYSIS, 2022, 12 (18) : 11152 - 11158
  • [45] Bronsted Acid Catalyzed Dearomatization by Intramolecular Hydroalkoxylation/Claisen Rearrangement: Diastereo- and Enantioselective Synthesis of Spirolactams
    Chen, Peng-Fei
    Zhou, Bo
    Wu, Peng
    Wang, Binju
    Ye, Long-Wu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (52) : 27164 - 27170
  • [46] Copper-Catalyzed Diastereo- and Enantioselective Desymmetrization of Cyclopropenes: Synthesis of Cyclopropylboronates
    Parra, Alejandro
    Amenos, Laura
    Guisan-Ceinos, Manuel
    Lopez, Aurora
    Garcia Ruano, Jose Luis
    Tortosa, Mariola
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (45) : 15833 - 15836
  • [47] Bifunctional-thiourea-catalyzed diastereo- and enantioselective aza-Henry reaction
    Xu, XN
    Furukawa, T
    Okino, T
    Miyabe, H
    Takemoto, Y
    CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (02) : 466 - 476
  • [48] Chiral Phosphoric Acid Catalyzed Diastereo- and Enantioselective Mannich-Type Reaction between Enamides and Thiazolones
    Kikuchi, Jun
    Momiyama, Norie
    Terada, Masahiro
    ORGANIC LETTERS, 2016, 18 (11) : 2521 - 2523
  • [49] Synthesis of Unsymmetrical Urea Derivatives via Cu-Catalyzed Reaction of Acylazide and Secondary Amine
    Shinde, Jivan
    Bhimrao Patil, Prakash
    Kavala, Veerababurao
    Yao, Ching-Fa
    CHEMISTRY & BIODIVERSITY, 2022, 19 (08)
  • [50] Cu-Catalyzed Enantioselective Hydrogermylation: Asymmetric Synthesis of Unnatural β-Germyl α-Amino Acids
    Lin, Weidong
    You, Lijun
    Yuan, Wei
    He, Chuan
    ACS CATALYSIS, 2022, 12 (23) : 14592 - 14600