Literature DB >> 16119933

Gold(I)-catalyzed synthesis of highly substituted furans.

Michael H Suhre1, Michael Reif, Stefan F Kirsch.   

Abstract

Cationic triphenylphosphinegold(I) complexes are excellent catalysts for a cascade reaction of propargyl-Claisen rearrangement and heterocyclization to synthesize tri- and tetrasubstituted furans. Starting from easily accessed propargyl vinyl ethers, the furans are obtained in 72-99% yield. [reaction: see text]

Entities:  

Year:  2005        PMID： 16119933     DOI： 10.1021/ol0514101

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  13 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.  Computation-guided development of Au-catalyzed cycloisomerizations proceeding via 1,2-Si or 1,2-H migrations: regiodivergent synthesis of silylfurans.

Authors:  Alexander S Dudnik; Yuanzhi Xia; Yahong Li; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2010-06-09       Impact factor: 15.419

3.  Gold(I)-Catalyzed Desymmetrization of 1,4-Dienes by an Enantioselective Tandem Alkoxylation/Claisen Rearrangement.

Authors:  Hongmiao Wu; Weiwei Zi; Guigen Li; Hongjian Lu; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-01       Impact factor: 15.336

Review 4.  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

5.  Metal-catalyzed 1,2-shift of diverse migrating groups in allenyl systems as a new paradigm toward densely functionalized heterocycles.

Authors:  Alexander S Dudnik; Anna W Sromek; Marina Rubina; Joseph T Kim; Alexander V Kel'in; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2008-01-04       Impact factor: 15.419

6.  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

Review 7.  Ligand effects in homogeneous Au catalysis.

Authors:  David J Gorin; Benjamin D Sherry; F Dean Toste
Journal:  Chem Rev       Date:  2008-07-25       Impact factor: 60.622

8.  Metal-catalyzed cascade rearrangements of 3-alkynyl flavone ethers.

Authors:  Yuan Xiong; Scott E Schaus; John A Porco
Journal:  Org Lett       Date:  2013-04-10       Impact factor: 6.005

9.  Gold(I)-catalyzed formation of furans by a Claisen-type rearrangement of ynenyl allyl ethers.

Authors:  Florin M Istrate; Fabien Gagosz
Journal:  Beilstein J Org Chem       Date:  2011-06-29       Impact factor: 2.883

10.  One-pot Diels-Alder cycloaddition/gold(I)-catalyzed 6-endo-dig cyclization for the synthesis of the complex bicyclo[3.3.1]alkenone framework.

Authors:  Boubacar Sow; Gabriel Bellavance; Francis Barabé; Louis Barriault
Journal:  Beilstein J Org Chem       Date:  2011-07-22       Impact factor: 2.883
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