Literature DB >> 20166668

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

Longwu Ye1, Li Cui, Guozhu Zhang, Liming Zhang.   

Abstract

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.

Entities:  

Year:  2010        PMID： 20166668      PMCID： PMC2847863          DOI： 10.1021/ja100041e

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  21 in total

1.  Rearrangement of alkynyl sulfoxides catalyzed by gold(I) complexes.

Authors:  Nathan D Shapiro; F Dean Toste
Journal:  J Am Chem Soc       Date:  2007-03-20       Impact factor: 15.419

Review 2.  Recent developments in the metal-catalyzed reactions of metallocarbenoids from propargylic esters.

Authors:  José Marco-Contelles; Elena Soriano
Journal:  Chemistry       Date:  2007       Impact factor: 5.236

Review 3.  Gold-catalyzed cycloisomerizations of enynes: a mechanistic perspective.

Authors:  Eloísa Jiménez-Núñez; Antonio M Echavarren
Journal:  Chem Rev       Date:  2008-07-18       Impact factor: 60.622

4.  Gas-phase synthesis and reactivity of a gold carbene complex.

Authors:  Alexey Fedorov; Marc-Etienne Moret; Peter Chen
Journal:  J Am Chem Soc       Date:  2008-06-19       Impact factor: 15.419

5.  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.

Authors:  John Watts; Alex Benn; Nick Flinn; Tracy Monk; Manoj Ramjee; Peter Ray; Yikang Wang; Martin Quibell
Journal:  Bioorg Med Chem       Date:  2004-06-01       Impact factor: 3.641

6.  Gold(I)-catalyzed intermolecular oxyarylation of alkynes: unexpected regiochemistry in the alkylation of arenes.

Authors:  Ana B Cuenca; Sergi Montserrat; Kabir M Hossain; Gisela Mancha; Agustí Lledós; Mercedes Medio-Simón; Gregori Ujaque; Gregorio Asensio
Journal:  Org Lett       Date:  2009-11-05       Impact factor: 6.005

7.  Geometry-dependent divergence in the gold-catalyzed redox cascade cyclization of o-alkynylaryl ketoximes and nitrones leading to isoindoles.

Authors:  Hyun-Suk Yeom; Youngun Lee; Ji-Eun Lee; Seunghoon Shin
Journal:  Org Biomol Chem       Date:  2009-09-01       Impact factor: 3.876

8.  Gold or no gold: one-pot synthesis of tetrahydrobenz[b]azepin-4-ones from tertiary N-(but-3-ynyl)anilines.

Authors:  Li Cui; Guozhu Zhang; Yu Peng; Liming Zhang
Journal:  Org Lett       Date:  2009-03-19       Impact factor: 6.005

9.  Gold(I) ethylene and copper(I) ethylene complexes supported by a polyhalogenated triazapentadienyl ligand.

Authors:  Jaime A Flores; H V Rasika Dias
Journal:  Inorg Chem       Date:  2008-04-23       Impact factor: 5.165

10.  Gold-catalyzed intramolecular redox reaction of sulfinyl alkynes: efficient generation of alpha-oxo gold carbenoids and application in insertion into R--CO bonds.

Authors:  Guotao Li; Liming Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336
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  43 in total

Review 1.  Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

Authors:  Anton V Gulevich; Alexander S Dudnik; Natalia Chernyak; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2013-01-10       Impact factor: 60.622

2.  Gold-catalyzed one-step practical synthesis of oxetan-3-ones from readily available propargylic alcohols.

Authors:  Longwu Ye; Weimin He; Liming Zhang
Journal:  J Am Chem Soc       Date:  2010-06-30       Impact factor: 15.419

3.  Rapid access to chroman-3-ones through gold-catalyzed oxidation of propargyl aryl ethers.

Authors:  Yanzhao Wang; Kegong Ji; Sylvester Lan; Liming Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2012-01-13       Impact factor: 15.336

4.  Umpolung reactivity of indole through gold catalysis.

Authors:  Biao Lu; Yingdong Luo; Lianzhu Liu; Longwu Ye; Yanzhao Wang; Liming Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-14       Impact factor: 15.336

5.  Gold-catalyzed nitrene transfer to activated alkynes: formation of α,β-unsaturated amidines.

Authors:  Chaoqun Li; Liming Zhang
Journal:  Org Lett       Date:  2011-02-25       Impact factor: 6.005

6.  Enantioselective oxidative gold catalysis enabled by a designed chiral P,N-bidentate ligand.

Authors:  Kegong Ji; Zhitong Zheng; Zhixun Wang; Liming Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2014-11-27       Impact factor: 15.336

7.  A Non-Diazo Strategy to Cyclopropanation via Oxidatively Generated Gold Carbene: the Benefit of A Conformationally Rigid P,N-Bidentate Ligand.

Authors:  Kegong Ji; Liming Zhang
Journal:  Org Chem Front       Date:  2014-03       Impact factor: 5.281

8.  Mechanism of gold(I)-catalyzed rearrangements of acetylenic amine-N-oxides: computational investigations lead to a new mechanism confirmed by experiment.

Authors:  Elizabeth L Noey; Yingdong Luo; Liming Zhang; K N Houk
Journal:  J Am Chem Soc       Date:  2011-12-22       Impact factor: 15.419

9.  Tempering the reactivities of postulated α-oxo gold carbenes using bidentate ligands: implication of tricoordinated gold intermediates and the development of an expedient bimolecular assembly of 2,4-disubstituted oxazoles.

Authors:  Yingdong Luo; Kegong Ji; Yuxue Li; Liming Zhang
Journal:  J Am Chem Soc       Date:  2012-10-11       Impact factor: 15.419

10.  Generation of rhodium(I) carbenes from ynamides and their reactions with alkynes and alkenes.

Authors:  Renhe Liu; Gabrielle N Winston-McPherson; Zhong-Yue Yang; Xin Zhou; Wangze Song; Ilia A Guzei; Xiufang Xu; Weiping Tang
Journal:  J Am Chem Soc       Date:  2013-05-23       Impact factor: 15.419
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