Nickel-catalyzed three-component [3+2+2] cocyclization of ethyl cyclopropylideneacetate and alkynes - Selective synthesis of multisubstituted cycloheptadienes

被引：109
作者：
Komagawa, S [1 ]
Saito, S [1 ]
机构：
[1] Tokyo Univ Sci, Dept Chem, Tokyo 1628601, Japan
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 15期
关键词：
alkynes; cycloaddition; cycloheptadienes; nickel; synthetic methods;
D O I：
10.1002/anie.200504050
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Chemical Equation Presented) Ménage à trois: Seven-membered carbocycles are formed by the three-component [3+2+2] cycloaddition of ethyl cyclopropylideneacetate and two different alkynes in the presence of a Ni 0/PPh3 catalyst (see scheme). In this one-pot reaction, a highly chemo- and regioselective coupling proceeds, and the cycloheptadiene derivatives are isolated as single isomers. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码：2446 / 2449
页数：4
相关论文
共 50 条
[41]   METALLACYCLOPENTANES AND BISOLEFIN COMPLEXES [J].
STOCKIS, A ;
HOFFMANN, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (09) :2952-2962
[42]   Selective preparation of pyridines, pyridones, and iminopyridines from two different alkynes via azazirconacycles [J].
Takahashi, T ;
Tsai, FY ;
Li, YZ ;
Wang, H ;
Kondo, Y ;
Yamanaka, M ;
Nakajima, K ;
Kotora, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (18) :5059-5067
[43]   Cycloaddition reaction of zirconacyclopentadienes to alkynes: Highly selective formation of benzene derivatives from three different alkynes [J].
Takahashi, T ;
Xi, ZF ;
Yamazaki, A ;
Liu, YH ;
Nakajima, K ;
Kotora, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (08) :1672-1680
[44]   Construction of pyridine rings by metal-mediated [2+2+2] cycloaddition [J].
Varela, JA ;
Saá, C .
CHEMICAL REVIEWS, 2003, 103 (09) :3787-3801
[45]  
Vollhardt K. P. C., 1984, ANGEW CHEM, V96, P525
[46]   COBALT-MEDIATED [2+2+2]-CYCLOADDITIONS - A MATURING SYNTHETIC STRATEGY [J].
VOLLHARDT, KPC .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (08) :539-556
[47]   COBALT METALLOCYCLES .6. PREPARATION AND STRUCTURE OF COBALTACYCLOPENTENE COMPLEXES AND THEIR REACTIONS WITH OLEFINS AND ACETYLENES [J].
WAKATSUKI, Y ;
AOKI, K ;
YAMAZAKI, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (05) :1123-1130
[48]   COBALT METALLACYCLES .11. ON THE TRANSFORMATION OF BIS(ACETYLENE)COBALT TO COBALTACYCLOPENTADIENE [J].
WAKATSUKI, Y ;
NOMURA, O ;
KITAURA, K ;
MOROKUMA, K ;
YAMAZAKI, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (07) :1907-1912
[49]   Three-component cycloadditions: The first transition metal-catalyzed [5+2+1] cycloaddition reactions [J].
Wender, PA ;
Gamber, GG ;
Hubbard, RD ;
Zhang, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (12) :2876-2877
[50]   TRANSITION-METAL-CATALYZED [5+2] CYCLOADDITIONS OF VINYLCYCLOPROPANES AND ALKYNES - A HOMOLOG OF THE DIELS-ALDER REACTION FOR THE SYNTHESIS OF 7-MEMBERED RINGS [J].
WENDER, PA ;
TAKAHASHI, H ;
WITULSKI, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (16) :4720-4721
12345