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
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
  • [1] Catalytic Enantioselective Friedel-Crafts Alkylation of Indoles with β,γ-Unsaturated α-Keto Phosphonates in the Presence of Chiral Palladium Complexes
    Kang, Young Ku
    Suh, Ki Hyung
    Kim, Dae Young
    SYNLETT, 2011, (08) : 1125 - 1128
  • [2] Designing new α,β-unsaturated thioesters for the catalytic, enantioselective Friedel-Crafts alkylation of indoles
    Bandini, M
    Melloni, A
    Tommasi, S
    Umani-Ronchi, A
    HELVETICA CHIMICA ACTA, 2003, 86 (11) : 3753 - 3763
  • [3] FRIEDEL-CRAFTS ALKYLATION OF INDOLES
    BUDYLIN, VA
    YERMOLENKO, MS
    KOST, AN
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1978, (07): : 921 - 924
  • [4] Catalytic enantioselective Friedel-Crafts alkylation of indoles with nitroalkenes by using a simple thiourea organocatalyst
    Herrera, RP
    Sgarzani, V
    Bernardi, L
    Ricci, A
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (40) : 6576 - 6579
  • [5] Friedel-Crafts alkylation of indoles with trichloroacetimidates
    Suzuki, Tamie
    Chisholm, John D.
    TETRAHEDRON LETTERS, 2019, 60 (19) : 1325 - 1329
  • [6] Enantioselective Friedel-Crafts Alkylation of Indoles, Pyrroles, and Furans with Trifluoropyruvate Catalyzed by Chiral Phosphoric Acid
    Kashikura, Wataru
    Itoh, Junji
    Mori, Keiji
    Akiyama, Takahiko
    CHEMISTRY-AN ASIAN JOURNAL, 2010, 5 (03) : 470 - 472
  • [7] CaSH Organocatalysis: Enantioselective Friedel-Crafts Alkylation of Indoles with α,β-Unsaturated Aldehydes
    Tian, Tian
    Pei, Bao-Jian
    Li, Qing-Hua
    He, Hao
    Chen, Ling-Yan
    Zhou, Xiang
    Chan, Wing-Hong
    Lee, Albert W. M.
    SYNLETT, 2009, (13) : 2115 - 2118
  • [8] Catalytic enantioselective Friedel-Crafts alkylations of indoles with α′-phosphoric enones
    Yang, Hyeyeon
    Hong, Young-Taek
    Kim, Sunggak
    ORGANIC LETTERS, 2007, 9 (12) : 2281 - 2284
  • [9] Synthesis of Tridentate Ligands Based on Chiral Diamines and Their Application to Enantioselective Friedel-Crafts Alkylation of Indoles with Nitroalkenes
    Wu Mei
    Wang Shoufeng
    Xia Chungu
    Sun Wei
    CHINESE JOURNAL OF CHEMISTRY, 2010, 28 (08) : 1424 - 1428
  • [10] Enantioselective Friedel-Crafts alkylation reaction of indoles with α,β-unsaturated acyl phosphonates catalyzed by chiral phosphoric acid
    Bachu, Prabhakar
    Akiyama, Takahiko
    CHEMICAL COMMUNICATIONS, 2010, 46 (23) : 4112 - 4114