Platinum(II)-Catalyzed Generation and [3+2] Cycloaddition Reaction of α,β-Unsaturated Carbene Complex Intermediates for the Preparation of Polycyclic Compounds

被引:90
作者
Saito, Kodai [1 ]
Sogou, Hideyuki [1 ]
Suga, Takuya [1 ]
Kusama, Hiroyuki [1 ]
Iwasawa, Nobuharu [1 ]
机构
[1] Tokyo Inst Technol, Dept Chem, Meguro Ku, Tokyo 1528551, Japan
关键词
CATALYZED CYCLOISOMERIZATION; PLATINUM CATALYSIS; PROPARGYLIC ESTERS; GOLD CATALYSIS; ENYNYL ESTERS; CYCLOPROPANATION; CARBOCYCLES; DIVERSITY; INDOLE;
D O I
10.1021/ja108586d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Pt(II)-catalyzed generation of unsaturated carbene complex intermediates from various propargyl ether derivatives based on electrophilic activation of alkynes was realized. These in situ generated unsaturated carbene complexes undergo [3+2] cycloaddition reaction with various vinyl ethers, leading to efficient formation of indoles, naphthols, and benzofuran fused with a five-membered ring in high yields.
引用
收藏
页码:689 / 691
页数:3
相关论文
共 30 条
[1]   Recent Advances in the Synthesis of Indole and Quinoline Derivatives through Cascade Reactions [J].
Barluenga, Jose ;
Rodriguez, Felix ;
Fananas, Francisco J. .
CHEMISTRY-AN ASIAN JOURNAL, 2009, 4 (07) :1036-1048
[2]   Platinum-catalyzed intramolecular hydroamination of unactivated olefins with secondary alkylamines [J].
Bender, CF ;
Widenhoefer, RA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (04) :1070-1071
[3]  
de Meijere A, 2000, ANGEW CHEM INT EDIT, V39, P3964, DOI 10.1002/1521-3773(20001117)39:22<3964::AID-ANIE3964>3.0.CO
[4]  
2-C
[5]   Fischer Carbene Complexes in Organic Synthesis: Metal-Assisted and Metal-Templated Reactions [J].
Doetz, Karl Heinz ;
Stendel, Joachim, Jr. .
CHEMICAL REVIEWS, 2009, 109 (08) :3227-3274
[6]   Catalytic carbophilic activation:: Catalysis by platinum and gold π acids [J].
Fuerstner, Alois ;
Davies, Paul W. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (19) :3410-3449
[7]   Gold and platinum catalysis-a convenient tool for generating molecular complexity [J].
Fuerstner, Alois .
CHEMICAL SOCIETY REVIEWS, 2009, 38 (11) :3208-3221
[8]   Gold(I)-catalyzed intramolecular acetylenic Schmidt reaction [J].
Gorin, DJ ;
Davis, NR ;
Toste, FD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (32) :11260-11261
[9]   Gold-catalyzed cycloisomerizations of enynes:: A mechanistic perspective [J].
Jimenez-Nunez, Eloisa ;
Echavarren, Antonio M. .
CHEMICAL REVIEWS, 2008, 108 (08) :3326-3350
[10]   Gold(I)-catalyzed stereoselective olefin cyclopropanation [J].
Johansson, MJ ;
Gorin, DJ ;
Staben, ST ;
Toste, FD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (51) :18002-18003