Preparation of helicenes through olefin metathesis

被引:124
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
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 [J].
Bonifacio, MC ;
Robertson, CR ;
Jung, JY ;
King, BT .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (21) :8522-8526
[2]   Efficient asymmetric synthesis of [7]helicene bisquinones [J].
Carreño, MC ;
González-López, M ;
Urbano, A .
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 [J].
Carreño, MC ;
García-Cerrada, S ;
Urbano, A .
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 [J].
Carreño, MC ;
García-Cerrada, S ;
Urbano, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (32) :7929-7930
[5]   Modified BINOL ligands in asymmetric catalysis [J].
Chen, Y ;
Yekta, S ;
Yudin, AK .
CHEMICAL REVIEWS, 2003, 103 (08) :3155-3211
[6]   Syntheses of [5]-helicene by McMurry or carbenoid couplings [J].
Dubois, F ;
Gingras, M .
TETRAHEDRON LETTERS, 1998, 39 (28) :5039-5040
[7]   Synthesis of carbohelicenes and derivatives by "carbenoid couplings" [J].
Gingras, M ;
Dubois, F .
TETRAHEDRON LETTERS, 1999, 40 (07) :1309-1312
[8]  
Grimme S, 1998, EUR J ORG CHEM, V1998, P1491
[9]   Olefin metathesis [J].
Grubbs, RH .
TETRAHEDRON, 2004, 60 (34) :7117-7140
[10]   [5]helicenes by tandem radical cyclisation [J].
Harrowven, DC ;
Nunn, MIT ;
Fenwick, DR .
TETRAHEDRON LETTERS, 2002, 43 (41) :7345-7347