Alkynes as equivalents of alpha-diazo ketones in generating alpha-oxo metal carbenes: a gold-catalyzed expedient synthesis of dihydrofuran-3-ones.

An expedient and reliable method for accessing reactive alpha-oxo gold carbenes via gold-catalyzed intermolecular oxidation of terminal alkynes has been developed. Significantly, this method offers a safe and economical alternative to the strategies based on diazo substrates. Its synthetic potential is demonstrated by expedient preparation of dihydrofuran-3-ones containing a broad range of functional groups.

[1]  Ji-Eun Lee,et al.  Geometry-dependent divergence in the gold-catalyzed redox cascade cyclization of o-alkynylaryl ketoximes and nitrones leading to isoindoles. , 2009, Organic & biomolecular chemistry.

[2]  P. Davies,et al.  Gold- or platinum-catalyzed synthesis of sulfur heterocycles: access to sulfur ylides without using sacrificial functionality. , 2009, Angewandte Chemie.

[3]  A. Lledós,et al.  Gold(I)-catalyzed intermolecular oxyarylation of alkynes: unexpected regiochemistry in the alkylation of arenes. , 2009, Organic letters.

[4]  Rai‐Shung Liu,et al.  Carbocyclisation of alkynes with external nucleophiles catalysed by gold, platinum and other electrophilic metals. , 2009, Chemical Society reviews.

[5]  Liming Zhang,et al.  A two-step, formal [4 + 2] approach toward piperidin-4-ones via Au catalysis. , 2009, Journal of the American Chemical Society.

[6]  M. M. Díaz‐Requejo,et al.  Gold-catalyzed olefin cyclopropanation , 2009 .

[7]  Liming Zhang,et al.  Gold or no gold: one-pot synthesis of tetrahydrobenz[b]azepin-4-ones from tertiary N-(but-3-ynyl)anilines. , 2009, Organic letters.

[8]  S. Nolan,et al.  Cationic NHC–gold(I) complexes: Synthesis, isolation, and catalytic activity , 2009 .

[9]  M. Fañanás‐Mastral,et al.  Carbene Transfer Reactions from Chromium(0) to Gold(I): Synthesis and Reactivity of New Fischer-Type Gold(I) Alkenyl Carbene Complexes , 2009 .

[10]  Ji-Eun Lee,et al.  Gold-catalyzed waste-free generation and reaction of azomethine ylides: internal redox/dipolar cycloaddition cascade. , 2008, Angewandte Chemie.

[11]  A. Echavarren,et al.  Gold-catalyzed cycloisomerizations of enynes: a mechanistic perspective. , 2008, Chemical reviews.

[12]  A. Fedorov,et al.  Gas-phase synthesis and reactivity of a gold carbene complex. , 2008, Journal of the American Chemical Society.

[13]  H. V. Rasika Dias,et al.  Gold(I) ethylene and copper(I) ethylene complexes supported by a polyhalogenated triazapentadienyl ligand. , 2008, Inorganic chemistry.

[14]  F. Gagosz,et al.  Synthesis and Reactivity of Air-Stable N-Heterocyclic Carbene Gold(I) Bis(trifluoromethanesulfonyl)imidate Complexes , 2007 .

[15]  Liming Zhang,et al.  Gold-catalyzed intramolecular redox reaction of sulfinyl alkynes: efficient generation of alpha-oxo gold carbenoids and application in insertion into R--CO bonds. , 2007, Angewandte Chemie.

[16]  S. Nolan,et al.  Propargylic esters in gold catalysis: access to diversity. , 2007, Angewandte Chemie.

[17]  N. Shapiro,et al.  Rearrangement of alkynyl sulfoxides catalyzed by gold(I) complexes. , 2007, Journal of the American Chemical Society.

[18]  E. Soriano,et al.  Recent developments in the metal-catalyzed reactions of metallocarbenoids from propargylic esters. , 2007, Chemistry.

[19]  Liming Zhang,et al.  Gold and platinum catalysis of enyne cycloisomerization , 2006 .

[20]  Zigang Li,et al.  Nitrene transfer reactions catalyzed by gold complexes. , 2006, The Journal of organic chemistry.

[21]  A. Echavarren,et al.  Gold-catalyzed intramolecular reaction of indoles with alkynes: facile formation of eight-membered rings and an unexpected allenylation. , 2006, Angewandte Chemie.

[22]  S. Nolan,et al.  A gold catalyst for carbene-transfer reactions from ethyl diazoacetate. , 2005, Angewandte Chemie.

[23]  F. Toste,et al.  Gold(I)-catalyzed intramolecular acetylenic Schmidt reaction. , 2005, Journal of the American Chemical Society.

[24]  Z. Gu,et al.  Gold-catalyzed cyclization of enynes. , 2005, Angewandte Chemie.

[25]  M. Ramjee,et al.  Functionalised 2,3-dimethyl-3-aminotetrahydrofuran-4-one and N-(3-oxo-hexahydrocyclopenta[b]furan-3a-yl)acylamide based scaffolds: synthesis and cysteinyl proteinase inhibition. , 2004, Bioorganic & medicinal chemistry.

[26]  H. Davies,et al.  Catalytic enantioselective C-H activation by means of metal-carbenoid-induced C-H insertion. , 2003, Chemical reviews.

[27]  G. Mehta,et al.  Tandem cyclization–cycloaddition reactions of rhodium generated carbenoids from α-diazo carbonyl compounds , 2002 .

[28]  A. Padwa,et al.  Synthetic applications of 1,3-dipolar cycloaddition chemistry toward heterocycles and natural products , 2002 .

[29]  T. Ye,et al.  Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides , 1998 .

[30]  J. Baldwin,et al.  Rules for ring closure. , 1977, Ciba Foundation symposium.

[31]  H. Jaffe,et al.  The Basicities of Substituted Pyridines and their 1-Oxides , 1955 .