Preparation of helicenes through olefin metathesis

被引：123
作者：
Collins, Shawn K. [1 ]
Grandbois, Alain [1 ]
Vachon, Martin P. [1 ]
Cote, Julie [1 ]
机构：
[1] Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 18期
关键词：
arenes; helical structures; helicenes; microwave irradiation; olefin metathesis;
D O I：
10.1002/anie.200504150
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Chemical Equation Presented) Metathesis with a twist! A ring-closing-metathesis strategy has been developed for the preparation of various substituted [5]helicene motifs and [6]- and [7]helicenes. The two optimized protocols include one method that utilizes the Grubbs second-generation catalyst under microwave-irradiation conditions and another that employs a modified Grubbs-Hoveyda catalyst at 40°C in a sealed reaction vessel. (Mes = mesityl). © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码：2923 / 2926
页数：4
相关论文
共 32 条
  • [1] Polycyclic aromatic hydrocarbons by ring-closing metathesis
    Bonifacio, MC
    Robertson, CR
    Jung, JY
    King, BT
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (21) : 8522 - 8526
  • [2] Efficient asymmetric synthesis of [7]helicene bisquinones
    Carreño, MC
    González-López, M
    Urbano, A
    [J]. CHEMICAL COMMUNICATIONS, 2005, (05) : 611 - 613
  • [3] From central to helical chirality:: Synthesis of P and M enantiomers of [5]helicenequinones and bisquinones from (SS)-2-(p-tolylsulfinyl)-1,4-benzoquinone
    Carreño, MC
    García-Cerrada, S
    Urbano, A
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (17) : 4118 - 4131
  • [4] Enantiopure dihydro-[5]-helicenequinones via Diels-Alder reactions of vinyl dihydrophenanthrenes and (SS)-2-(p-tolylsulfinyl)-1,4-benzoquinone
    Carreño, MC
    García-Cerrada, S
    Urbano, A
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (32) : 7929 - 7930
  • [5] Modified BINOL ligands in asymmetric catalysis
    Chen, Y
    Yekta, S
    Yudin, AK
    [J]. CHEMICAL REVIEWS, 2003, 103 (08) : 3155 - 3211
  • [6] Syntheses of [5]-helicene by McMurry or carbenoid couplings
    Dubois, F
    Gingras, M
    [J]. TETRAHEDRON LETTERS, 1998, 39 (28) : 5039 - 5040
  • [7] Synthesis of carbohelicenes and derivatives by "carbenoid couplings"
    Gingras, M
    Dubois, F
    [J]. TETRAHEDRON LETTERS, 1999, 40 (07) : 1309 - 1312
  • [8] Grimme S, 1998, EUR J ORG CHEM, V1998, P1491
  • [9] Olefin metathesis
    Grubbs, RH
    [J]. TETRAHEDRON, 2004, 60 (34) : 7117 - 7140
  • [10] [5]helicenes by tandem radical cyclisation
    Harrowven, DC
    Nunn, MIT
    Fenwick, DR
    [J]. TETRAHEDRON LETTERS, 2002, 43 (41) : 7345 - 7347
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