Ruthenium-Catalyzed [2+2+2] Cocyclization of Diene-yne

被引:50
作者
Tanaka, Daisuke
Sato, Yoshihiro
Mori, Miwako [1 ]
机构
[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan
[2] Hlth Sci Hokkaido Univ, Ishikari, Hokkaido 0610293, Japan
关键词
D O I
10.1021/ja071954t
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Ruthenium-catalyzed [2 + 2 + 2] cocyclization of diene-yne was developed. The reaction conditions were very mild; that is, a toluene solution of diene-yne was stirred in the presence of 5 mol % of Cp*Ru(cod)Cl. Tricyclic carbo- or heterocycles were obtained in high yields from corresponding straight carbon-chain compounds.
引用
收藏
页码:7730 / +
页数:3
相关论文
共 20 条
[1]   [2+2+2] cycloaddition reactions catalyzed by transition metal complexes [J].
Chopade, Pramod R. ;
Louie, Janis .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (16-17) :2307-2327
[2]  
Grotjahn D. B, 1995, COMPREHENSIVE ORGANO, V12, P741
[3]   Novel synthesis of benzenepolycarboxylates by ruthenium-catalyzed cross-benzannulation of acetylenedicarboxylates with allylic compounds [J].
Kondo, T ;
Kaneko, Y ;
Tsunawaki, F ;
Okada, T ;
Shiotsuki, M ;
Morisaki, Y ;
Mitsudo, TA .
ORGANOMETALLICS, 2002, 21 (21) :4564-4567
[4]   Transition metal catalyzed [2+2+2] cycloaddition and application in organic synthesis [J].
Kotha, S ;
Brahmachary, E ;
Lahiri, K .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (22) :4741-4767
[5]   Novel alkenylative cyclization using a ruthenium catalyst [J].
Mori, M ;
Saito, N ;
Tanaka, D ;
Takimoto, M ;
Sato, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (19) :5606-5607
[6]   Transition-metal-catalyzed reactions in heterocyclic synthesis [J].
Nakamura, I ;
Yamamoto, Y .
CHEMICAL REVIEWS, 2004, 104 (05) :2127-2198
[7]   SYNTHESIS AND SOME REACTIONS OF DICHLORO(PENTAMETHYLCYCLOPENTADIENYL)RUTHENIUM(III) OLIGOMER [J].
OSHIMA, N ;
SUZUKI, H ;
MOROOKA, Y .
CHEMISTRY LETTERS, 1984, (07) :1161-1164
[8]   Recent advances in the transition-metal-catalyzed regioselective approaches to polysubstituted benzene derivatives [J].
Saito, S ;
Yamamoto, Y .
CHEMICAL REVIEWS, 2000, 100 (08) :2901-2915
[9]   Novel chemoselectivity and stereochemical aspects of nickel-catalyzed [2+2+2] cycloadditions [J].
Seo, J ;
Chui, HMP ;
Heeg, MJ ;
Montgomery, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (02) :476-477
[10]   Enantioselective intramolecular [2+2+2] cycloaddition of 1,4-diene-ynes: A new approach to the construction of quaternary carbon stereocenters [J].
Shibata, Takanori ;
Tahara, Yu-ki .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (36) :11766-11767