CHIRAL PHOSPHORIC ACID CATALYZED ASYMMETRIC FRIEDEL-CRAFTS ALKYLATION OF INDOLES WITH NITROOLEFINS

被引：9
作者：
Tang, Hong-Ying [1 ]
Zhang, Zhong-Biao [1 ]
机构：
[1] Tianjin Normal Univ, Tianjin Key Lab Water Environm & Resources, Tianjin 300387, Peoples R China
来源：
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 2011年 / 186卷 / 10期
关键词：
Asymmetric Friedel-Crafts alkylations; enantioselectivities; chiral phosphoric acid; indoles; nitroolefins; TETRAHYDRO-BETA-CARBOLINES; BOND-FORMING REACTIONS; BRONSTED ACID; ENANTIOSELECTIVE ADDITION; NITROALKENES; COMPLEXES; IMINES; ORGANOCATALYSTS; BIS(OXAZOLINE); DISCOVERY;
D O I：
10.1080/10426507.2010.536189
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Asymmetric Michael-type Friedel-Crafts (F-C) alkylations of indoles with nitroolefins catalyzed by a chiral H-8-BINOL-based phosphoric acid were investigated. The reactions took place very smoothly in the presence of only 5 mol-% of catalyst at room temperature to afford the desired F-C alkylation products in good yields and with moderate enantioselectivities.
引用
收藏
页码：2038 / 2046
页数：9
相关论文
共 43 条
  • [1] Adair G, 2008, ALDRICHIM ACTA, V41, P31
  • [2] Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid
    Akiyama, T
    Itoh, J
    Yokota, K
    Fuchibe, K
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) : 1566 - 1568
  • [3] Stronger bronsted acids
    Akiyama, Takahiko
    [J]. CHEMICAL REVIEWS, 2007, 107 (12) : 5744 - 5758
  • [4] Recent progress in chiral Bronsted acid catalysis
    Akiyama, Takahiko
    Itoh, Junji
    Fuchibe, Kohei
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (09) : 999 - 1010
  • [5] Tandem catalytic asymmetric Friedel-Crafts/Henry reaction: Control of three contiguous acyclic stereocenters
    Arai, Takayoshi
    Yokoyama, Naota
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (27) : 4989 - 4992
  • [6] A library of chiral imidazoline-aminophenol ligands: Discovery of an efficient reaction sphere
    Arai, Takayoshi
    Yokoyama, Naota
    Yanagisawa, Akira
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (07) : 2052 - 2059
  • [7] Catalytic enantioselective addition of indoles to arylnitroalkenes: An effective route to enantiomerically enriched tryptamine precursors
    Bandini, M
    Garelli, A
    Rovinetti, M
    Tommasi, S
    Umani-Ronchi, A
    [J]. CHIRALITY, 2005, 17 (09) : 522 - 529
  • [8] A journey across recent advances in catalytic and stereoselective alkylation of indoles
    Bandini, M
    Melloni, A
    Tommasi, S
    Umani-Ronchi, A
    [J]. SYNLETT, 2005, (08) : 1199 - 1222
  • [9] 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
  • [10] Catalytic Functionalization of Indoles in a New Dimension
    Bandini, Marco
    Eichholzer, Astrid
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (51) : 9608 - 9644
12345