Preparation of substituted cyclopentadienes through platinum(II)-catalyzed cyclization of 1,2,4-trienes

被引:113
作者
Funami, Hideaki [1 ]
Kusama, Hiroyuki [1 ]
Iwasawa, Nobuharu [1 ]
机构
[1] Tokyo Inst Technol, Dept Chem, Meguro Ku, Tokyo 1528551, Japan
关键词
allenes; carbenes; cyclopentadienes; platinum; synthetic methods;
D O I
10.1002/anie.200603986
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) A pinch of platinum... Platinum(II)-catalyzed cyclization of 1,2,4-trienes proceeds under mild conditions to give well-defined, highly substituted cyclopentadienes in good yield. The reaction was confirmed to proceed through α,β-unsaturated platinum-carbene complex intermediates (see scheme). © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:909 / 911
页数:3
相关论文
共 38 条
[1]  
[Anonymous], DIELSALDER REACTION
[2]   Nucleophilic transition metal based cyclization of allenes [J].
Bates, RW ;
Satcharoen, V .
CHEMICAL SOCIETY REVIEWS, 2002, 31 (01) :12-21
[3]   MULTIPLE SEX-CHROMOSOMES IN THE GENUS HOPLIAS (PISCES, ERYTHRINIDAE) [J].
BERTOLLO, LAC ;
TAKAHASHI, CS ;
MOREIRA, O .
CYTOLOGIA, 1983, 48 (01) :1-12
[4]   Gold(I) catalyzed isomerization of 5-en-2-yn-1-yl acetates: An efficient access to acetoxy bicyclo[3.1.0]hexenes and 2-cycloalken-1-ones [J].
Buzas, Andrea ;
Gagosz, Fabien .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) :12614-12615
[5]   PtCl2-catalyzed conversion of 1,6- and 1,7-enynes to 1-vinylcycloalkenes. Anomalous bond connection in skeletal reorganization of enynes [J].
Chatani, N ;
Furukawa, N ;
Sakurai, H ;
Murai, S .
ORGANOMETALLICS, 1996, 15 (03) :901-903
[6]   Ruthenium-catalyzed cycloisomerization of cis-3-en-1-ynes to cyclopentadiene and related derivatives through a 1,5-sigmatropic hydrogen shift of ruthenium-vinylidene intermediates [J].
Datta, S ;
Odedra, A ;
Liu, RS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (33) :11606-11607
[7]   Formation of cyclopentadiene derivatives by reaction of zirconacyclopentadienes with 1,1-dihalo compounds [J].
Duan, Z ;
Sun, WH ;
Liu, YH ;
Takahashi, T .
TETRAHEDRON LETTERS, 2000, 41 (39) :7471-7474
[8]   Non-stabilized transition metal carbenes as intermediates in intramolecular reactions of alkynes with alkenes [J].
Echavarren, AM ;
Nevado, C .
CHEMICAL SOCIETY REVIEWS, 2004, 33 (07) :431-436
[9]   Reaction of aluminacyclopentadienes with aldehydes affording cyclopentadiene derivatives [J].
Fang, HY ;
Zhao, CJ ;
Li, GT ;
Xi, ZF .
TETRAHEDRON, 2003, 59 (21) :3779-3786
[10]   SYNTHESIS AND APPLICATIONS OF CHIRAL CYCLOPENTADIENYLMETAL COMPLEXES [J].
HALTERMAN, RL .
CHEMICAL REVIEWS, 1992, 92 (05) :965-994