Friedel-Crafts-type alkylation in aqueous media using resin-supported peptide catalyst having polyleucine

被引:34
作者
Akagawa, Kengo [1 ]
Yamashita, Takuhiro [1 ]
Sakamoto, Seiji [2 ]
Kudo, Kazuaki [1 ]
机构
[1] Univ Tokyo, Inst Ind Sci, Meguro Ku, Tokyo 1538505, Japan
[2] Tohoku Univ, Inst Multidisciplinary Res Adv Mat, Aoba Ku, Sendai, Miyagi 9808577, Japan
关键词
ASYMMETRIC TRANSFER HYDROGENATION; CYCLIC 1,3-DICARBONYL COMPOUNDS; INDOLE ALKYLATIONS; CONSTRUCTION; ORGANOCATALYSTS; NITROALKENES; PYRROLE; ALKENES; SILICA;
D O I
10.1016/j.tetlet.2009.07.071
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The asymmetric Friedel-Crafts-type alkylation in aqueous media was realized by the resin-supported N-terminal prolyl peptide catalyst having a polyleucine tether. The hydrophobic polyleucine chain in the peptide catalyst was essential for the reaction efficiency and enantioselectivity. The resin-bound peptide catalyst could be reused at least for five times. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5602 / 5604
页数:3
相关论文
共 44 条
  • [1] Organocatalytic asymmetric transfer hydrogenation in aqueous media using resin-supported peptide having a polyleucine tether
    Akagawa, Kengo
    Akabane, Hajime
    Sakamoto, Seiji
    Kudo, Kazuaki
    [J]. ORGANIC LETTERS, 2008, 10 (10) : 2035 - 2037
  • [2] Asymmetric transfer hydrogenation in aqueous media catalyzed by resin-supported peptide having a polyleucine tether
    Akagawa, Kengo
    Akabane, Hajime
    Sakamoto, Seiji
    Kudo, Kazuaki
    [J]. TETRAHEDRON-ASYMMETRY, 2009, 20 (04) : 461 - 466
  • [3] Enantioselective organocatalytic construction of pyrroloindolines by a cascade addition-cyclization strategy: Synthesis of (-)-flustramine B
    Austin, JF
    Kim, SG
    Sinz, CJ
    Xiao, WJ
    MacMillan, DWC
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) : 5482 - 5487
  • [4] Enantioselective organocatalytic indole alkylations. Design of a new and highly effective chiral amine for iminium catalysis
    Austin, JF
    MacMillan, DWC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (07) : 1172 - 1173
  • [5] 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
  • [6] 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
  • [7] 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
  • [8] Aziridin-2-yl methanols as organocatalysts in Diels-Alder reactions and Friedel-Crafts alkylations of N-methyl-pyrrole and N-methyl-indole
    Bonini, Bianca F.
    Capito, Elena
    Comes-Franchini, Mauro
    Fochi, Mariafrancesca
    Riccia, Alfredo
    Zwanenburg, Binne
    [J]. TETRAHEDRON-ASYMMETRY, 2006, 17 (22) : 3135 - 3143
  • [9] Chiral pyrrolidinium salts as organocatalysts in the stereoselective 1,4-conjugate addition of N-methylpyrrole to cyclopent-1-ene carbaldehyde
    Breistein, P
    Karlsson, S
    Hedenström, E
    [J]. TETRAHEDRON-ASYMMETRY, 2006, 17 (01) : 107 - 111
  • [10] Organocatalytic enantioselective indole alkylations of α,β-unsaturated ketones
    Chen, Wei
    Du, Wei
    Yue, Lei
    Li, Rui
    Wu, Yong
    Ding, Li-Sheng
    Chen, Ying-Chun
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (05) : 816 - 821