Enantioselective Friedel-Crafts Alkylation of Indoles with β,γ- Unsaturated α-Ketoesters Catalyzed by New Copper(I) Catalysts

被引：14
作者：
Yu, Shibo [1 ,2 ]
Cai, Qihang [1 ,2 ]
Wang, Chao [1 ,2 ]
Hou, Jiaqi [1 ,2 ]
Liang, Jiemian [1 ,2 ]
Jiao, Zilin [1 ,2 ]
Yao, Chao [1 ,2 ]
Li, Yue-Ming [1 ,2 ]
机构：
[1] Nankai Univ, Coll Pharm, State Key Lab Med Chem Biol, Tianjin 300350, Peoples R China
[2] Nankai Univ, Tianjin Key Lab Mol Drug Res, Tianjin 300350, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 05期
基金：
中国国家自然科学基金;
关键词：
ACID CATALYSIS; PYRROLE; DESIGN;
D O I：
10.1021/acs.joc.2c02749
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
New Cu(I) catalysts are effective in enantioselective Friedel-Crafts alkylation of a variety of indoles with different beta,gamma- unsaturated alpha-ketoesters. A control study shows that such a catalyst system is less sensitive to air, and the reactions can be carried out without special cares such as glovebox operation or moisture/oxygen-free conditions. Preliminary computation results suggest that there exists pi-pi stacking between the substrate and the catalyst, and such an interaction seems to play a role in stabilizing the reaction intermediate and enhancing the stereoselectivity of the reactions. The desired products can be obtained in up to 98% yield at 99% enantiomeric excess. The same high enantioselectivity can be observed when the reaction is carried in a gram scale, indicating a good scalability of the catalyst system in enantioselective Friedel-Crafts alkylation of different indoles with beta,gamma-unsaturated alpha-ketoesters.
引用
收藏
页码：3046 / 3053
页数：8
相关论文
共 40 条
  • [1] Alexakis A, 2014, COPPER-CATALYZED ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/9783527664573
  • [2] Kinetic resolution of epoxides by a C-C bond-forming reaction:: Highly enantioselective addition of indoles to cis, trans, and meso aromatic epoxides catalyzed by [Cr(salen)] complexes
    Bandini, M
    Cozzi, PG
    Melchiorre, P
    Umani-Ronchi, A
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (01) : 84 - 87
  • [3] New catalytic approaches in the stereoselective Friedel-Crafts alkylation reaction
    Bandini, M
    Melloni, A
    Umani-Ronchi, A
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (05) : 550 - 556
  • [4] Synthesis of strychnine
    Bonjoch, J
    Solé, D
    [J]. CHEMICAL REVIEWS, 2000, 100 (09) : 3455 - 3482
  • [5] Synthetic approaches to natural products containing 2,3-dihydrobenzofuran skeleton
    Chen, Zhuang
    Pitchakuntla, Mallesham
    Jia, Yanxing
    [J]. NATURAL PRODUCT REPORTS, 2019, 36 (04) : 666 - 690
  • [6] Tuning the Copper(II)/Copper(I) Redox Potential for More Robust Copper-Catalyzed C-N Bond Forming Reactions
    Cope, James D.
    Valle, Henry U.
    Hall, Ruby S.
    Riley, Kathleen M.
    Goel, Ekta
    Biswas, Saborni
    Hendrich, Michael P.
    Wipf, David O.
    Stokes, Sean L.
    Emerson, Joseph P.
    [J]. EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2020, 2020 (14) : 1278 - 1285
  • [7] Stereo- and Regioselective [3+3] Annulation Reaction Catalyzed by Ytterbium: Synthesis of Bicyclic 1,4-Dihydropyridines
    del Corte, Xabier
    Lopez-Frances, Adrian
    de Marigorta, Edorta Martinez
    Palacios, Francisco
    Vicario, Javier
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (20) : 4761 - 4769
  • [8] Further developments of β,γ-unsaturated α-ketoesters as versatile synthons in asymmetric catalysis
    Deng, Ruixian
    Han, Tian-Jiao
    Gao, Xiang
    Yang, Yuan-Fu
    Mei, Guang-Jian
    [J]. ISCIENCE, 2022, 25 (03)
  • [9] Substituted (E)-2-Oxo-3-butenoates: Reagents for Every Enantioselectively-Catalyzed Reaction
    Desimoni, Giovanni
    Faita, Giuseppe
    Quadrelli, Paolo
    [J]. CHEMICAL REVIEWS, 2013, 113 (08) : 5924 - 5988
  • [10] Catalytic Enantioselective Additions of Indoles to Nitroalkenes
    Ganesh, Madhu
    Seidel, Daniel
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (49) : 16464 - +
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