(Pentamethylcyclopentadienyl)Iridium Dichloride Dimer {[IrCp*Cl2]2}: A Novel Efficient Catalyst for the Cycloisomerizations of Homopropargylic Diols and N-Tethered Enynes

被引:35
作者
Benedetti, Erica [1 ,2 ]
Simonneau, Antoine [1 ]
Hours, Alexandra [1 ]
Amouri, Hani [1 ]
Penoni, Andrea [2 ]
Palmisano, Giovanni [2 ]
Malacria, Max [1 ]
Goddard, Jean-Philippe [1 ]
Fensterbank, Louis [1 ]
机构
[1] UPMC Univ Paris 06, Inst Parisien Chim Mol, CNRS, IUMR 7201,FR 2769, F-75005 Paris, France
[2] Univ Insubria, Dipartimento Sci Chim & Ambientali, I-22100 Como, Italy
关键词
bicyclic compounds; cycloisomerization; enynes; homogeneous catalysis; iridium(III); CATIONIC GOLD(I) COMPLEXES; TERMINAL ALKYNES; ATOM ECONOMY; OXIDATIVE CYCLIZATION; PLATINUM CATALYSIS; BICYCLIC KETALS; IDEAL SYNTHESIS; BOND FORMATION; ALCOHOLS; IRIDIUM;
D O I
10.1002/adsc.201100124
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
(Pentamethylcyclopentadienyl)iridium dichloride dimer {[IrCp*Cl-2](2)}-catalyzed hydroalkoxylation of bis-homopropargylic alcohols provides an efficient access to dioxabicyclo[2.2.1]ketals. The cycloisomerizations proceed under mild conditions, with low catalytic loadings and short reaction times. This new protocol involving an Ir(III) catalyst also promoted the cycloisomerization of nitrogen-tethered 1,6-enynes to give azabicyclo[4.1.0]heptenes, enhancing the synthetic potential of our method.
引用
收藏
页码:1908 / 1912
页数:5
相关论文
共 78 条
[1]  
[Anonymous], 2009, Angew. Chem
[2]   Highly efficient access to strained bicyclic ketals via gold-catalyzed cycloisomerization of bis-homopropargylic diols [J].
Antoniotti, S ;
Genin, E ;
Michelet, V ;
Genêt, JP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (28) :9976-9977
[3]  
Antoniotti S., 2005, ANGEW CHEM, V117, P5029
[4]   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
[5]   Gold(I)-Catalyzed Cyclization of β-Allenylhydrazones: An Efficient Synthesis of Multisubstituted N-Aminopyrroles [J].
Benedetti, Erica ;
Lemiere, Gilles ;
Chapellet, Laure-Lise ;
Penoni, Andrea ;
Palmisano, Giovanni ;
Malacria, Max ;
Goddard, Jean-Philippe ;
Fensterbank, Louis .
ORGANIC LETTERS, 2010, 12 (19) :4396-4399
[6]   A NOVEL PTCL4-CATALYZED CYCLOREARRANGEMENT OF ALLYL PROPYNYL ETHERS TO 3-OXABICYCLO[4.1.0]HEPTENES [J].
BLUM, J ;
BEERKRAFT, H ;
BADRIEH, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (17) :5567-5569
[7]   Platinum(II) Catalysts for Highly Enantioselective 1,6-Enyne Cycloisomerizations. Synthetic, Structural, and Catalytic Studies [J].
Brissy, Delphine ;
Skander, Myriem ;
Jullien, Helene ;
Retailleau, Pascal ;
Marinetti, Angela .
ORGANIC LETTERS, 2009, 11 (10) :2137-2139
[8]   Asymmetric Au(I)-catalyzed synthesis of bicyclo[4.1.0]heptene derivatives via a cycloisomerization process of 1,6-enynes [J].
Chao, Chung-Meng ;
Beltrami, Denis ;
Toullec, Patrick Y. ;
Michelet, Veronique .
CHEMICAL COMMUNICATIONS, 2009, (45) :6988-6990
[9]   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
[10]   Iridium(I)-catalyzed cycloisomerization of enynes [J].
Chatani, N ;
Inoue, H ;
Morimoto, T ;
Muto, T ;
Murai, S .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (12) :4433-4436