Divergent mechanisms for the skeletal rearrangement and [2+2] cycloaddition of enynes catalyzed by gold.

Support for the direct route: That cyclobutenes are not necessary intermediates in the skeletal rearrangement of enynes is supported by DFT calculations and kinetic studies. Cyclobutenes may arise from the corresponding syn-cyclopropylgold(I) carbenes

[1]  A. Fürstner,et al.  Cyclobutenes by platinum-catalyzed cycloisomerization reactions of enynes. , 2005, Journal of the American Chemical Society.

[2]  E. Soriano,et al.  Theoretical Investigation on the Mechanisms of the PtCl2-Mediated Cycloisomerization of Polyfunctionalized 1,6-Enynes. 1. Role of the Propargylic Substituents , 2005 .

[3]  A. Echavarren,et al.  Intramolecular [4 + 2] cycloadditions of 1,3-enynes or arylalkynes with alkenes with highly reactive cationic phosphine Au(I) complexes. , 2005, Journal of the American Chemical Society.

[4]  A. Echavarren,et al.  Ligand Effects in Gold- and Platinum-Catalyzed Cyclization of Enynes: Chiral Gold Complexes for Enantioselective Alkoxycyclization , 2005 .

[5]  G. B. Bajracharya,et al.  PtBr2-catalyzed consecutive enyne metathesis-aromatization of 1-(1-methoxy-but-3-enyl)-2-(1-alkynyl)benzenes: dual role of the Pt catalyst. , 2005, The Journal of organic chemistry.

[6]  C. Nevado,et al.  Non-stabilized transition metal carbenes as intermediates in intramolecular reactions of alkynes with alkenes. , 2004, Chemical Society reviews.

[7]  Liming Zhang,et al.  Gold-catalyzed cycloisomerization of siloxy enynes to cyclohexadienes. , 2004, Journal of the American Chemical Society.

[8]  F. Toste,et al.  Catalytic isomerization of 1,5-enynes to bicyclo[3.1.0]hexenes. , 2004, Journal of the American Chemical Society.

[9]  A. Fürstner,et al.  Platinum- and gold-catalyzed cycloisomerization reactions of hydroxylated enynes. , 2004, Journal of the American Chemical Society.

[10]  C. Nevado,et al.  Cationic gold(I) complexes: highly alkynophilic catalysts for the exo- and endo-cyclization of enynes. , 2004, Angewandte Chemie.

[11]  L. Fensterbank,et al.  Platinum dichloride-catalyzed cycloisomerization of ene-ynamides. , 2004, Organic letters.

[12]  S. Diver,et al.  Enyne metathesis (enyne bond reorganization). , 2004, Chemical reviews.

[13]  C. Nevado,et al.  Reaction of enol ethers with alkynes catalyzed by transition metals: 5-exo-dig versus 6-endo-dig cyclizations via cyclopropyl platinum or gold carbene complexes. , 2003, Chemistry.

[14]  K. Houk,et al.  Altering the allowed/forbidden gap in cyclobutene electrocyclic reactions: experimental and theoretical evaluations of the effect of planarity constraints. , 2003, Journal of the American Chemical Society.

[15]  G. Lloyd‐Jones.  Mechanistic aspects of transition metal catalysed 1,6-diene and 1,6-enyne cycloisomerisation reactions. , 2003, Organic & biomolecular chemistry.

[16]  H. Inoue,et al.  Skeletal reorganization of enynes to 1-vinylcycloalkenes catalyzed by GaCl(3). , 2002, Journal of the American Chemical Society.

[17]  M. Malacria,et al.  The behavior of 1,n-enynes in the presence of transition metals. , 2002, Chemical reviews.

[18]  Gabriel Oba,et al.  Stereoselective polycyclisations of allyl and enyne silanes: evidence for a bicyclo[3.2.0]hept-1(7)ene structure , 2002 .

[19]  F. Stelzer,et al.  Platinum-catalyzed cycloisomerization reactions of enynes. , 2001, Journal of the American Chemical Society.

[20]  C. Nevado,et al.  Cyclizations of enynes catalyzed by PtCl2 or other transition metal chlorides: divergent reaction pathways. , 2001, Journal of the American Chemical Society.

[21]  D. Tantillo,et al.  Complicated goings-on in the metal-manipulated ring-opening of cyclobutene. , 2001, Journal of the American Chemical Society.

[22]  Y. Inoue,et al.  Cationic Platinum-Complex-Catalyzed Skeletal Reorganization of Enynes , 2001 .

[23]  H. Inoue,et al.  Iridium(I)-catalyzed cycloisomerization of enynes. , 2001, The Journal of organic chemistry.

[24]  B. Trost,et al.  A Pd-Catalyzed (2 + 2) Cycloaddition. Mechanism of a Pd-Catalyzed Enyne Metathesis. , 1993 .

[25]  B. Trost,et al.  Mechanistic dichotomies in Pd catalyzed enyne metathesis of cyclic olefins , 1991 .

[26]  G. Geier,et al.  Coordination chemistry of gold(I) with cyanide and 1-methylpyridine-2-thione. Kinetics and thermodynamics of ligand exchange at gold(I) in aqueous solution , 1988 .

[27]  B. Trost,et al.  An unusual mechanism of a palladium-catalyzed intramolecular carbametalation. A novel palladium-catalyzed rearrangement , 1988 .

[28]  W. Maier,et al.  Additions and Corrections - Evaluation and Prediction of the Stability of Bridgehead Olefins. , 1981 .

[29]  C. Oh,et al.  PtCl₄-catalyzed Cycloreorganization of 1,6- and 1,7-Enynes , 2003 .