Catalytic Enantioselective Friedel-Crafts Alkylation of Indoles with Fumarate Derivatives in the Presence of Chiral Palladium Complexes

被引：23
|
作者：
Lee, Hyun Joo [1 ]
Kim, Dae Young [1 ]
机构：
[1] Soonchunhyang Univ, Dept Chem, Asan 336745, Chungnam, South Korea
来源：
SYNLETT | 2012年 / 11期
关键词：
Friedel-Crafts reaction; asymmetric catalysis; chiral palladium catalysts; indoles; fumamate derivatives; MANNICH-TYPE REACTIONS; BETA-KETO-ESTERS; CONJUGATE ADDITION; ALPHA; BETA-UNSATURATED KETONES; CARBONYL-COMPOUNDS; ACID CATALYSIS; ASYMMETRIC-SYNTHESIS; ALPHA-HYDROXYLATION; MICHAEL ADDITION; PHOSPHORIC-ACID;
D O I：
10.1055/s-0031-1290424
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The catalytic enantioselective Friedel-Crafts alkylation reaction promoted by chiral palladium complexes is described. The treatment of indoles with fumarate derivatives under the mild reaction conditions afforded the corresponding Friedel-Crafts alkylation adducts with high enantioselectivities (up to 91% ee).
引用
收藏
页码：1629 / 1632
页数：4
相关论文
共 50 条
  • [41] Synthesis of Magnetic Nanoparticles and Polymer Supported Imidazolidinone Catalysts for Enantioselective Friedel-Crafts Alkylation of Indoles
    Pagoti, Sreenivasarao
    Ghosh, Tridev
    Dash, Jyotirmayee
    CHEMISTRYSELECT, 2016, 1 (15): : 4386 - 4391
  • [42] Dianhydrohexitols: new tools for organocatalysis. Application in enantioselective Friedel-Crafts alkylation of indoles with nitroalkenes
    Chen, Ling-Yan
    Guillarme, Stephane
    Saluzzo, Christine
    ARKIVOC, 2013, : 227 - 244
  • [43] Enantioselective Friedel-Crafts Alkylation of Indoles with Aromatic α,β-Unsaturated Aldehydes Catalyzed by Diphenylprolinol Silyl Ether
    Wang, Zhi-Jing
    Yang, Jian-Guo
    Jin, Jun
    Lv, Xin
    Bao, Weiliang
    SYNTHESIS-STUTTGART, 2009, (23): : 3994 - 4000
  • [44] Enantioselective Friedel-Crafts Alkylation of Indoles with β,γ- Unsaturated α-Ketoesters Catalyzed by New Copper(I) Catalysts
    Yu, Shibo
    Cai, Qihang
    Wang, Chao
    Hou, Jiaqi
    Liang, Jiemian
    Jiao, Zilin
    Yao, Chao
    Li, Yue-Ming
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (05): : 3046 - 3053
  • [45] Chiral Bis(Oxazolinyl)thiophenes for Enantioselective Cu(II)-Catalyzed Friedel-Crafts Alkylation of Indole Derivatives with Nitroalkenes
    Li, Weijie
    CATALYSIS LETTERS, 2014, 144 (05) : 943 - 948
  • [46] FRIEDEL-CRAFTS ALKYLATION REACTION CATALYSTS AND COMPLEXES
    BROWN, HC
    PEARSALL, HW
    EDDY, LP
    WALLACE, WJ
    GRAYSON, M
    NELSON, KL
    INDUSTRIAL AND ENGINEERING CHEMISTRY, 1953, 45 (07): : 1462 - 1469
  • [47] Stereoselective Double Friedel-Crafts Alkylation of Indoles with Divinyl Ketones
    Silvanus, Andrew C.
    Heffernan, Stephen J.
    Liptrot, David J.
    Kociok-Koehn, Gabriele
    Andrews, Benjamin I.
    Carbery, David R.
    ORGANIC LETTERS, 2009, 11 (05) : 1175 - 1178
  • [48] Organocatalytic Enantioselective Friedel-Crafts Aminoalkylation of Indoles in the Carbocyclic Ring
    Montesinos-Magraner, Marc
    Vila, Carlos
    Rendon-Patino, Alejandra
    Blay, Gonzalo
    Fernandez, Isabel
    Munoz, M. Carmen
    Pedro, Jose R.
    ACS CATALYSIS, 2016, 6 (04): : 2689 - 2693
  • [49] Highly Enantioselective Friedel-Crafts-type Alkylation Reactions of Indoles with Chalcone Derivatives using a Chiral Barium Catalyst
    Tsubogo, Tetsu
    Kano, Yuichiro
    Yamashita, Yasuhiro
    Kobayashi, Shu
    CHEMISTRY-AN ASIAN JOURNAL, 2010, 5 (09) : 1974 - 1977
  • [50] Ammonium chiral borate salt catalyzed asymmetric Friedel-Crafts alkylation of indoles with α,β-disubstituted enals
    Ueda, Mitsuhiro
    Yagyu, Yoshitaka
    Ryu, Ilhyong
    TETRAHEDRON-ASYMMETRY, 2017, 28 (08) : 1070 - 1077
12345