Non-metathesis reactions of ruthenium carbene catalysts and their application to the synthesis of nitrogen-containing heterocycles

被引:48
作者
Arisawa, Mitsuhiro
Terada, Yukiyoshi
Takahashi, Kazuyuki
Nakagawa, Masako
Nishida, Atsushi
机构
[1] Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
[2] Hokkaido Univ, Grad Sch Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan
[3] Kanagawa Univ, Fac Sci, Dept Chem, Kanagawa 2591293, Japan
关键词
ruthenium; isomerization; cycloisomerization; heterocycles; indole;
D O I
10.1002/tcr.20121
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Non-metathesis reactions of ruthenium carbene catalysts, such as olefin isomerization, hydrogenation, radical reaction, activation of silane, cyclopropanation, epimerization cocyclopropane, [3 + 2] cycloaddition, and cycloisomerization, are summarized. The utility of these reactions was demonstrated by the synthesis of indole using olefin isomerization and subsequent ring-closing metathesis, the synthesis of indoline using cycloisomerization, and the synthesis of the putative structure of fistulosin using cycloisomerization as a key step. (c) 2007 The Japan Chemical Journal Forum and Wiley Periodicals, Inc.
引用
收藏
页码:238 / 253
页数:16
相关论文
共 93 条
[1]   Two birds with one metallic stone: Single-pot catalysis of fundamentally different transformations [J].
Ajamian, A ;
Gleason, JL .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (29) :3754-3760
[2]   Ruthenium-catalyzed chemoselective N-allyl cleavage: Novel Grubbs carbene mediated deprotection of allylic amines [J].
Alcaide, B ;
Almendros, P ;
Alonso, JM .
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (23) :5793-5799
[3]   Non-metathetic behavior patterns of Grubbs' carbene [J].
Alcaide, B ;
Almendros, P .
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (06) :1259-1262
[4]   Novel ruthenium-catalyzed cleavage of allyl protecting group in lactams [J].
Alcaide, B ;
Almendros, P ;
Alonso, JM .
TETRAHEDRON LETTERS, 2003, 44 (48) :8693-8695
[5]   A novel use of Grubbs' carbene. Application to the catalytic deprotection of tertiary allylamines [J].
Alcaide, B ;
Almendros, P ;
Alonso, JM ;
Aly, MF .
ORGANIC LETTERS, 2001, 3 (23) :3781-3784
[6]   Regio- and stereoselective hydrosilylation of terminal alkynes using Grubbs' first-generation olefin-metathesis catalyst [J].
Aricó, CS ;
Cox, LR .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (18) :2558-2562
[7]   Preparation of N-sulfonyl-2-quinolinone using ring-closing metathesis(RCM) [J].
Arisawa, M ;
Theeraladanon, C ;
Nishida, A .
HETEROCYCLES, 2005, 66 :683-688
[8]   Development of novel reactions using ruthenium carbene catalyst and its application to novel methods for preparing nitrogen-containing heterocycles [J].
Arisawa, M ;
Terada, Y ;
Theeraladanon, C ;
Takahashi, K ;
Nakagawa, M ;
Nishida, A .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (24-25) :5398-5406
[9]   Selective isomerization of a terminal olefin catalyzed by a ruthenium complex: The synthesis of indoles through ring-closing metathesis [J].
Arisawa, M ;
Terada, Y ;
Nakagawa, M ;
Nishida, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (24) :4732-4734
[10]   Stereoselectivity in ring-closing olefin metathesis (RCM) of tethered dihexenoyl derivatives [J].
Arisawa, M ;
Kaneko, H ;
Nishida, A ;
Nakagawa, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (07) :959-964