Literature DB >> 16986931

Golden times for allenes: Gold-catalyzed cycloisomerization of beta-hydroxyallenes to dihydropyrans.

Birgit Gockel1, Norbert Krause.   

Abstract

The gold(I)-catalyzed 6-endo cycloisomerization of beta-hydroxyallenes provides a mild and efficient access to chiral functionalized dihydropyrans which were obtained at room temperature in good chemical yields with axis-to-center chirality transfer. The method was extended to the beta-aminoallene 12, which afforded tetrahydropyridine 13 in good yield as well.

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Year:  2006        PMID: 16986931     DOI: 10.1021/ol061669z

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


  9 in total

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

Authors:  Pablo Mauleón; Jamin L Krinsky; F Dean Toste
Journal:  J Am Chem Soc       Date:  2009-04-01       Impact factor: 15.419

2.  Mechanistic insights into the gold-catalyzed cycloisomerization of bromoallenyl ketones: ligand-controlled regioselectivity.

Authors:  Yuanzhi Xia; Alexander S Dudnik; Vladimir Gevorgyan; Yahong Li
Journal:  J Am Chem Soc       Date:  2008-05-08       Impact factor: 15.419

Review 3.  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

4.  Dinuclear gold-silver resting states may explain silver effects in gold(I)-catalysis.

Authors:  Dieter Weber; Michel R Gagné
Journal:  Org Lett       Date:  2009-11-05       Impact factor: 6.005

5.  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

6.  Bifunctionalized Allenes. Part XVI. Synthesis of 3-Phosphoryl-2,5-dihydrofurans by Coinage Metal-Catalyzed Cyclo-isomerization of Phosphorylated α-Hydroxyallenes.

Authors:  Valerij Ch Christov; Ismail E Ismailov; Ivaylo K Ivanov
Journal:  Molecules       Date:  2015-04-21       Impact factor: 4.411

7.  Palladium-catalyzed oxidative acyloxylation/carbocyclization of allenynes.

Authors:  Youqian Deng; Jan-E Bäckvall
Journal:  Angew Chem Int Ed Engl       Date:  2013-02-05       Impact factor: 15.336

8.  Stereodivergent synthesis of jaspine B and its isomers using a carbohydrate-derived alkoxyallene as C3-building block.

Authors:  Volker Martin Schmiedel; Stefano Stefani; Hans-Ulrich Reissig
Journal:  Beilstein J Org Chem       Date:  2013-11-19       Impact factor: 2.883

9.  Micellar catalysis-enabled sustainable ppm Au-catalyzed reactions in water at room temperature.

Authors:  Piyatida Klumphu; Camille Desfeux; Yitao Zhang; Sachin Handa; Fabrice Gallou; Bruce H Lipshutz
Journal:  Chem Sci       Date:  2017-07-20       Impact factor: 9.825

  9 in total

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