Literature DB >> 20161695

Gold(I)-catalyzed synthesis of (1E,3E)-dienes from propargylic esters.

Alexander S Dudnik1, Todd Schwier, Vladimir Gevorgyan.   

Abstract

A mild and stereoselective gold(I)-catalyzed domino transformation of propargylic esters leading to substituted (1E,3E)-dienes has been developed. This cascade process proceeds via a sequence of 1,3-acyloxy- or 1,3-phosphatyloxy migrations to form allenic intermediate followed by a proton transfer.

Entities:  

Year:  2009        PMID： 20161695      PMCID： PMC2678727          DOI： 10.1016/j.jorganchem.2008.08.010

Source DB:  PubMed          Journal:  J Organomet Chem        ISSN： 0022-328X            Impact factor:   2.369


  30 in total

1.  Gold(I)-catalyzed stereoselective formation of functionalized 2,5-dihydrofurans.

Authors:  Andrea Buzas; Florin Istrate; Fabien Gagosz
Journal:  Org Lett       Date:  2006-04-27       Impact factor: 6.005

Review 2.  Relativistic effects in homogeneous gold catalysis.

Authors:  David J Gorin; F Dean Toste
Journal:  Nature       Date:  2007-03-22       Impact factor: 49.962

3.  Gold-catalyzed organic reactions.

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

4.  Gold catalysts: towards sustainable chemistry.

Authors:  Tamao Ishida; Masatake Haruta
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

5.  Pd(OAc)2-catalyzed coupling/cyclization of 2,3-allenoic acids and methyl propiolate: observation of double 1,7-hydrogen shifts.

Authors:  Zhenhua Gu; Shengming Ma
Journal:  Angew Chem Int Ed Engl       Date:  2006-09-11       Impact factor: 15.336

6.  Brønsted acid catalyzed addition of phenols, carboxylic acids, and tosylamides to simple olefins.

Authors:  Zigang Li; Junliang Zhang; Chad Brouwer; Cai-Guang Yang; Nicholas W Reich; Chuan He
Journal:  Org Lett       Date:  2006-09-14       Impact factor: 6.005

7.  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

8.  Gold-catalyzed efficient preparation of linear alpha-iodoenones from propargylic acetates.

Authors:  Meng Yu; Guozhu Zhang; Liming Zhang
Journal:  Org Lett       Date:  2007-04-28       Impact factor: 6.005

9.  Mechanistically diverse copper-, silver-, and gold-catalyzed acyloxy and phosphatyloxy migrations: efficient synthesis of heterocycles via cascade migration/cycloisomerization approach.

Authors:  Todd Schwier; Anna W Sromek; Dahrika M L Yap; Dmitri Chernyak; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2007-07-21       Impact factor: 15.419

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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  5 in total

1.  Copper-, Silver-, and Gold-Catalyzed Migratory Cycloisomerizations Leading to Heterocyclic Five-Membered Rings.

Authors:  Alexander S Dudnik; Natalia Chernyak; Vladimir Gevorgyan
Journal:  Aldrichimica Acta       Date:  2010       Impact factor: 3.667

2.  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

3.  Synthesis of highly functionalized cyclohexenone rings: rhodium-catalyzed 1,3-acyloxy migration and subsequent [5+1] cycloaddition.

Authors:  Dongxu Shu; Xiaoxun Li; Min Zhang; Patrick J Robichaux; Weiping Tang
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-29       Impact factor: 15.336

4.  Stereocontrolled 1,3-phosphatyloxy and 1,3-halogen migration relay toward highly functionalized 1,3-dienes.

Authors:  Roohollah Kazem Shiroodi; Alexander S Dudnik; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2012-04-12       Impact factor: 15.419

Review 5.  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
  5 in total

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