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
  • [11] Enantioselective Friedel-Crafts Alkylation Reaction of Indoles with α-Trifluoromethylated β-Nitrostyrenes Catalyzed by Chiral BINOL Metal Phosphate
    Ibanez, Ignacio
    Kaneko, Mio
    Kamei, Yuto
    Tsutsumi, Ryosuke
    Yamanaka, Masahiro
    Akiyama, Takahiko
    ACS CATALYSIS, 2019, 9 (08) : 6903 - 6909
  • [12] Selective Friedel-Crafts alkylation of indoles with trichloroacetimidates
    Suzuki, Tamie
    Adhikari, Arijit
    Chisholm, John
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256
  • [13] An Efficient Enantioselective Method for Asymmetric Friedel-Crafts Alkylation of Indoles with α,β-Unsaturated Aldehydes
    Hong, Liang
    Wang, Lei
    Chen, Chao
    Zhang, Bangzhi
    Wang, Rui
    ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (05) : 772 - 778
  • [14] Nickel-Catalyzed Enantioselective Friedel-Crafts Alkylation of Indoles with ,-Disubstituted Nitroalkenes
    Wu, Hao
    Sheng, Wei-Jian
    Chen, Bin
    Liu, Ren-Rong
    Gao, Jian-Rong
    Jia, Yi-Xia
    SYNLETT, 2015, 26 (20) : 2817 - 2820
  • [15] Catalytic enantioselective Friedel-Crafts/Michael addition reactions of indoles to ethenetricarboxylates
    Yamazaki, S
    Iwata, Y
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (02): : 739 - 743
  • [16] CHIRAL PHOSPHORIC ACID CATALYZED ASYMMETRIC FRIEDEL-CRAFTS ALKYLATION OF INDOLES WITH NITROOLEFINS
    Tang, Hong-Ying
    Zhang, Zhong-Biao
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2011, 186 (10) : 2038 - 2046
  • [17] Asymmetric Friedel-Crafts Alkylation of Indoles Catalyzed by Chiral Aziridine-Phosphines
    Buchcic, Aleksandra
    Zawisza, Anna
    Lesniak, Stanislaw
    Rachwalski, Michal
    CATALYSTS, 2020, 10 (09)
  • [18] Catalytic Enantioselective Friedel-Crafts Allenylation
    Das, Priyotosh
    Ghosh, Debangshu
    Mukherjee, Santanu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (47)
  • [19] Highly enantioselective Friedel-Crafts reaction of indoles with imines by a chiral phosphoric acid
    Kang, Qiang
    Zhao, Zhuo-An
    You, Shu-Li
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (06) : 1484 - +
  • [20] Highly Enantioselective Friedel-Crafts Alkylation/N-Hemiacetalization Cascade Reaction with Indoles
    Cheng, Hong-Gang
    Lu, Liang-Qiu
    Wang, Tao
    Yang, Qing-Qing
    Liu, Xiao-Peng
    Li, Yang
    Deng, Qiao-Hui
    Chen, Jia-Rong
    Xiao, Wen-Jing
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (11) : 3250 - 3254
12345