Asymmetric Construction of Polycyclic Indoles through Olefin Cross-Metathesis/Intramolecular Friedel-Crafts Alkylation under Sequential Catalysis

被引:160
作者
Cai, Quan [1 ]
Zhao, Zhuo-An [1 ]
You, Shu-Li [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
asymmetric catalysis; chiral Bronsted acids; Friedel-Crafts alkylation; indoles; sequential catalysis; TETRAHYDRO-BETA-CARBOLINES; PICTET-SPENGLER REACTIONS; CHIRAL PHOSPHORIC-ACIDS; BRONSTED ACID; COOPERATIVE CATALYSIS; STEREOSELECTIVE ALKYLATION; ENANTIOSELECTIVE SYNTHESIS; RELAY CATALYSIS; METAL CATALYSIS; 4,7-DIHYDROINDOLES;
D O I
10.1002/anie.200903462
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A synthetic shortcut: A highly efficient cascade reaction (see scheme) led to polycyclic indoles with excellent enantioselectivity. The combination of the two steps through sequential catalysis enables the use of more readily available starting materials and makes the synthesis more practical. Boc=tert- butoxycarbonyl. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:7428 / 7431
页数:4
相关论文
共 69 条
  • [11] Can simple enones be useful partners for the catalytic stereoselective alkylation of indoles?
    Bandini, M
    Fagioli, M
    Garavelli, M
    Melloni, A
    Trigari, V
    Umani-Ronchi, A
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (22) : 7511 - 7518
  • [12] 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
  • [13] BANDINI M, 2004, ANGEW CHEM, V176, P560
  • [14] Organocatalytic asymmetric Friedel-Crafts alkylation of indoles with simple α,β-unsaturated ketones
    Bartoli, Giuseppe
    Bosco, Marcella
    Carlone, Armando
    Pesciaioli, Fabio
    Sambri, Letizia
    Melchiorre, Paolo
    [J]. ORGANIC LETTERS, 2007, 9 (07) : 1403 - 1405
  • [15] Chapman C. J., 2007, SYNTHESIS, P1
  • [16] Chen J.R., 2008, Angew. Chem., V120, P2523
  • [17] Ru-catalyzed tandem cross-metathesis/intramolecular-hydroarylation sequence
    Chen, Jia-Rong
    Li, Chang-Feng
    An, Xiao-Lei
    Zhang, Ji-Ji
    Zhu, Xiao-Yu
    Xiao, Wen-Jing
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (13) : 2489 - 2492
  • [18] Chiral phosphoric acids: Powerful organocatalysts for asymmetric addition reactions to imines
    Connon, Stephen J.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (24) : 3909 - 3912
  • [19] THE PICTET-SPENGLER CONDENSATION - A NEW DIRECTION FOR AN OLD REACTION
    COX, ED
    COOK, JM
    [J]. CHEMICAL REVIEWS, 1995, 95 (06) : 1797 - 1842
  • [20] Enders D., 2007, Angew. Chem, V119, P1590, DOI DOI 10.1002/ange.200603129