Literature DB >> 19275228

Mechanistic studies on Au(I)-catalyzed [3,3]-sigmatropic rearrangements using cyclopropane probes.

Pablo Mauleón1, Jamin L Krinsky, F Dean Toste.   

Abstract

A comparative study of the Au(I)-catalyzed [3,3]-sigmatropic rearrangement of propargylic esters and propargyl vinyl ethers is described. Stereochemically defined cyclopropanes are employed as mechanistic probes to provide new synthetic and theoretical data concerning the reversibility of this type of rearrangement. Factors controlling the structure-reactivity relationship of Au(I)-coordinated allenes have been examined, thereby allowing for controlled access to orthogonal reactivity.

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Year:  2009        PMID： 19275228      PMCID： PMC2666792          DOI： 10.1021/ja900456m

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


  53 in total

1.  Golden carousel in catalysis: the cationic gold/propargylic ester cycle.

Authors:  Andrea Correa; Nicolas Marion; Louis Fensterbank; Max Malacria; Steven P Nolan; Luigi Cavallo
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

2.  Gold-catalyzed organic reactions.

Authors:  A Stephen K Hashmi
Journal:  Chem Rev       Date:  2007-06-20       Impact factor: 60.622

3.  Gold(I)-catalyzed [2 + 2]-cycloaddition of allenenes.

Authors:  Michael R Luzung; Pablo Mauleón; F Dean Toste
Journal:  J Am Chem Soc       Date:  2007-09-21       Impact factor: 15.419

4.  Total synthesis of the antibiotic erypoegin H and cognates by a PtCl2-catalyzed cycloisomerization reaction.

Authors:  Alois Fürstner; Eike K Heilmann; Paul W Davies
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

5.  Tandem gold(I)-catalyzed cyclization/electrophilic cyclopropanation of vinyl allenes.

Authors:  Gilles Lemière; Vincent Gandon; Kevin Cariou; Takahide Fukuyama; Anne-Lise Dhimane; Louis Fensterbank; Max Malacria
Journal:  Org Lett       Date:  2007-04-25       Impact factor: 6.005

6.  DFT study of the mechanisms of in water Au(I)-catalyzed tandem [3,3]-rearrangement/Nazarov reaction/[1,2]-hydrogen shift of enynyl acetates: a proton-transport catalysis strategy in the water-catalyzed [1,2]-hydrogen shift.

Authors:  Fu-Qiang Shi; Xin Li; Yuanzhi Xia; Liming Zhang; Zhi-Xiang Yu
Journal:  J Am Chem Soc       Date:  2007-11-21       Impact factor: 15.419

7.  Alkyne versus allene activation in platinum- and gold-catalyzed cycloisomerization of hydroxylated 1,5-allenynes.

Authors:  Riadh Zriba; Vincent Gandon; Corinne Aubert; Louis Fensterbank; Max Malacria
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

8.  Gold-catalyzed hydrative carbocyclization of 1,5- and 1,7-allenynes mediated by pi-allene complex: mechanistic evidence supported by the chirality transfer of allenyne substrates.

Authors:  Chun-Yao Yang; Guan-You Lin; Hsin-Yi Liao; Swarup Datta; Rai-Shung Liu
Journal:  J Org Chem       Date:  2008-06-04       Impact factor: 4.354

9.  Gold-catalyzed cyclization of allene-substituted malonate esters: synthesis of beta,gamma-unsaturated delta-lactones.

Authors:  Julio Piera; Patrik Krumlinde; Dirk Strübing; Jan-E Bäckvall
Journal:  Org Lett       Date:  2007-04-28       Impact factor: 6.005

10.  Gold-catalyzed double migration-benzannulation cascade toward naphthalenes.

Authors:  Alexander S Dudnik; Todd Schwier; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2008-03-01       Impact factor: 6.005
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  23 in total

1.  The use of Br/Cl to promote regioselective gold-catalyzed rearrangement of propargylic carboxylates: an efficient synthesis of (1Z, 3E)-1-bromo/chloro-2-carboxy-1,3-dienes.

Authors:  Yanzhao Wang; Biao Lu; Liming Zhang
Journal:  Chem Commun (Camb)       Date:  2010-10-29       Impact factor: 6.222

2.  Mechanistic surprises in the gold(I)-catalyzed intramolecular hydroarylation of allenes.

Authors:  Dieter Weber; Michael A Tarselli; Michel R Gagné
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

3.  Rhodium-catalyzed ring expansion of cyclopropanes to seven-membered rings by 1,5 C-C bond migration.

Authors:  Xiaoxun Li; Min Zhang; Dongxu Shu; Patrick J Robichaux; Suyu Huang; Weiping Tang
Journal:  Angew Chem Int Ed Engl       Date:  2011-09-09       Impact factor: 15.336

4.  Mechanistic study of gold(I)-catalyzed intermolecular hydroamination of allenes.

Authors:  Z Jane Wang; Diego Benitez; Ekaterina Tkatchouk; William A Goddard; F Dean Toste
Journal:  J Am Chem Soc       Date:  2010-09-22       Impact factor: 15.419

Review 5.  Rhodium-catalyzed acyloxy migration of propargylic esters in cycloadditions, inspiration from the recent "gold rush".

Authors:  Xing-Zhong Shu; Dongxu Shu; Casi M Schienebeck; Weiping Tang
Journal:  Chem Soc Rev       Date:  2012-12-07       Impact factor: 54.564

6.  A Reactivity-Driven Approach to the Discovery and Development of Gold-Catalyzed Organic Reactions.

Authors:  Nathan D Shapiro; F Dean Toste
Journal:  Synlett       Date:  2010-03-01       Impact factor: 2.454

Review 7.  Metal-catalyzed double migratory cascade reactions of propargylic esters and phosphates.

Authors:  Roohollah Kazem Shiroodi; Vladimir Gevorgyan
Journal:  Chem Soc Rev       Date:  2013-06-21       Impact factor: 54.564

8.  Gold-catalyzed transannular [4+3] cycloaddition reactions.

Authors:  Benjamin W Gung; Derek T Craft; Lauren N Bailey; Kristin Kirschbaum
Journal:  Chemistry       Date:  2010-01-11       Impact factor: 5.236

9.  Regio- and stereoselective synthesis of fluoroalkenes by directed Au(I) catalysis.

Authors:  Benjamin C Gorske; Curren T Mbofana; Scott J Miller
Journal:  Org Lett       Date:  2009-10-01       Impact factor: 6.005

10.  On the impact of steric and electronic properties of ligands on gold(I)-catalyzed cycloaddition reactions.

Authors:  Diego Benitez; Ekaterina Tkatchouk; Ana Z Gonzalez; William A Goddard; F Dean Toste
Journal:  Org Lett       Date:  2009-11-05       Impact factor: 6.005
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