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
[21]   Au-catalyzed reaction of propargylic sulfides and dithioacetals [J].
Peng, Lingling ;
Zhang, Xiu ;
Zhang, Shiwei ;
Wang, Jianbo .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (04) :1192-1197
[22]   2-CYCLOPENTENONES FROM 1-ETHYNYL-2-PROPENYL ACETATES [J].
RAUTENSTRAUCH, V .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (05) :950-952
[23]   Synthesis of Diverse Indole-Containing Scaffolds by Gold(I)-Catalyzed Tandem Reactions of 3-Propargylindoles Initiated by 1,2-Indole Migrations: Scope and Computational Studies [J].
Sanz, Roberto ;
Miguel, Delia ;
Gohain, Mukut ;
Garcia-Garcia, Patricia ;
Fernandez-Rodriguez, Manuel A. ;
Gonzalez-Perez, Adan ;
Nieto-Faza, Olalla ;
de Lera, Angel R. ;
Rodriguez, Felix .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (32) :9818-9828
[24]   Synthesis of azepines by a gold-catalyzed intermolecular [4+3]-annulation [J].
Shapiro, Nathan D. ;
Toste, F. Dean .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) :9244-+
[25]   Gold-Catalyzed [3+3]-Annulation of Azomethine Imines with Propargyl Esters [J].
Shapiro, Nathan D. ;
Shi, Yun ;
Toste, F. Dean .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (33) :11654-+
[26]   Recent advances in syntheses of carbocycles and heterocycles via homogeneous gold catalysis. Part 2: Cyclizations and cycloadditions [J].
Shen, Hong C. .
TETRAHEDRON, 2008, 64 (34) :7847-7870
[27]   Cationic Rhodium(I) Complex-Catalyzed [3+2] and [2+1] Cycloadditions of Propargyl Esters with Electron-Deficient Alkynes and Alkenes [J].
Shibata, Yu ;
Noguchi, Keiichi ;
Tanaka, Ken .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (23) :7896-+
[28]   Au-containing all-carbon 1,3-dipoles: Generation and [3+2] cycloaddition reactions [J].
Zhang, Guozhu ;
Zhang, Liming .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (38) :12598-+
[29]   Gold and platinum catalysis of enyne cycloisomerization [J].
Zhang, Liming ;
Sun, Jianwei ;
Kozmin, Sergey A. .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (16-17) :2271-2296
[30]   Pt-Catalyzed Tandem 1,2-Acyloxy Migration/Intramolecular [3+2] Cycloaddition of Enynyl Esters [J].
Zheng, Huaiji ;
Zheng, Jiyue ;
Yu, Binxun ;
Chen, Qiang ;
Wang, Xiaolei ;
He, Yongping ;
Yang, Zhen ;
She, Xuegong .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (06) :1788-+