(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

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2011年 / 353卷 / 11-12期

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

页码：1908 / 1912

页数：5

共 78 条

[31] An efficient low-temperature route to polycyclic isoquinoline salt synthesis via C-H activation with [Cp☆MCl2]2 (M = Rh, Ir) [J].

Li, Ling ;

Brennessel, William W. ;

Jones, William D. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (37) :12414-12419

[32] Recent Mechanistic and Synthetic Developments in the Chemistry of Transition-Metal Vinylidene Complexes [J].

Lynam, Jason M. .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (28) :8238-8247

[33] Gold- and Platinum-Catalyzed Cycloisomerization of Enynyl Esters versus Allenenyl Esters: An Experimental and Theoretical Study [J].

Marion, Nicolas ;

Lemiere, Gilles ;

Correa, Andrea ;

Costabile, Chiara ;

Ramon, Ruben S. ;

Moreau, Xavier ;

de Fremont, Pierre ;

Dahmane, Rim ;

Hours, Alexandra ;

Lesage, Denis ;

Tabet, Jean-Claude ;

Goddard, Jean-Philippe ;

Gandon, Vincent ;

Cavallo, Luigi ;

Fensterbank, Louis ;

Malacria, Max ;

Nolan, Steven P. .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (13) :3243-3260

[34] Stereoselective glycosylations of a family of 6-deoxy-1,2-glycals generated by catalytic alkynol cycloisomerization [J].

McDonald, FE ;

Reddy, KS ;

Díaz, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (18) :4304-4309

[35] Tungsten carbonyl-induced cyclizations of alkynyl alcohols to dihydropyranylidene carbenes and alpha-stannyl dihydropyrans [J].

McDonald, FE ;

Bowman, JL .

TETRAHEDRON LETTERS, 1996, 37 (27) :4675-4678

[36] Discovery of the tungsten carbonyl-catalyzed endo-selective alkynyl alcohol cycloisomerization reaction:: applications to stereoselective syntheses of D-olivose, D-olivose disaccharide substructures of landomycin and mithramycin [J].

McDonald, FE ;

Reddy, KS .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 617 (01) :444-452

[37] Cyclizations of enynes catalyzed by PtCl2 or other transition metal chlorides:: Divergent reaction pathways [J].

Méndez, M ;

Muñoz, MP ;

Nevado, C ;

Cárdenas, DJ ;

Echavarren, AM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (43) :10511-10520

[38] Rhodium- and iridium-catalyzed double hydroalkoxylation of alkynes, an efficient method for the synthesis of O,O-acetals:: Catalytic and mechanistic studies [J].

Messerle, Barbara A. ;

Vuong, Khuong Q. .

ORGANOMETALLICS, 2007, 26 (12) :3031-3040

[39]

Michelet V., 2008, ANGEW CHEM, V120, P4338

[40] Cycloisomerization of 1,n-enynes:: Challenging metal-catalyzed rearrangements and mechanistic insights [J].

Michelet, Veronique ;

Toullec, Patrick Y. ;

Genet, Jean-Pierre .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (23) :4268-4315

← 1 2 3 4 5 6 7 8 →