(N-Heterocyclic carbene) Gold(I)-Catalyzed cycloisomerization of cyclohexadienyl Alkynes to Tetracyclo[3.3.0.02,8.04,6] octanes

被引:77
作者
Kim, Soo Min [1 ]
Park, Ji Hoon [1 ]
Choi, Soo Young [1 ]
Chung, Young Keun [1 ]
机构
[1] Coll Nat Sci, Intelligent Text Syst Res Ctr, Dept Chem, Seoul 151747, South Korea
关键词
cycloisomerization; enynes; gold; strained ringcompounds;
D O I
10.1002/anie.200702028
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Biscyclopropanation: Dienynes containing a cyclohexadienyl unit can be converted into tetracyclo[3.3.0.0 2,8.04,6]-octanes by treatment with an (N-heterocyclic carbene)gold catalyst. When the dienynes bear an open-chain diene instead of cyclohexadiene, open-cage compounds, with two sides missing from the cage, are obtained. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:6172 / 6175
页数:4
相关论文
共 41 条
[1]  
[Anonymous], ANGEW CHEM
[2]   F-block N-heterocyclic carbene complexes [J].
Arnold, Polly L. ;
Liddle, Stephen T. .
CHEMICAL COMMUNICATIONS, 2006, (38) :3959-3971
[3]   The behavior of 1,n-enynes in the presence of transition metals [J].
Aubert, C ;
Buisine, O ;
Malacria, M .
CHEMICAL REVIEWS, 2002, 102 (03) :813-834
[4]   Electrophilic activation and cycloisomerization of enynes: A new route to functional cyclopropanes [J].
Bruneau, C .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (16) :2328-2334
[5]   Chiral N-heterocyclic carbenes as stereodirecting ligands in asymmetric catalysis [J].
César, V ;
Bellemin-Laponnaz, S ;
Gade, LH .
CHEMICAL SOCIETY REVIEWS, 2004, 33 (09) :619-636
[6]  
Couty S., 2006, ANGEW CHEM, V118, P6878
[7]   Diastereoselective gold-catalyzed cycloisomerizations of ene-ynamides [J].
Couty, Sylvain ;
Meyer, Christophe ;
Cossy, Janine .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (40) :6726-6730
[8]   NHC ligands versus cyclopentadienyls and phosphines as spectator ligands in organometallic catalysis [J].
Crabtree, RH .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (24-25) :5451-5457
[9]   Stability and reactivity of N-heterocyclic carbene complexes [J].
Crudden, CM ;
Allen, DP .
COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2247-2273