Literature DB >> 15250710

PtCl2-catalyzed cycloisomerizations of 5-en-1-yn-3-ol systems.

Youssef Harrak1, Christophe Blaszykowski, Matthieu Bernard, Kevin Cariou, Emily Mainetti, Virginie Mouriès, Anne-Lise Dhimane, Louis Fensterbank, Max Malacria.   

Abstract

5-En-1-yn-3-ol substrates bearing a free hydroxyl group or an acyl group are highly versatile partners for PtCl2-catalyzed cycloisomerizations. Electrophilic activation of the alkyne moiety triggers at wish a hydride or an O-acyl migration yielding at the end to regioisomeric keto derivatives. The efficient preparation of Sabina ketone, an important monoterpene precursor, has been worked out.

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Year:  2004        PMID： 15250710     DOI： 10.1021/ja0474695

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


  24 in total

1.  Well-Defined Chiral Gold(III) Complex Catalyzed Direct Enantioconvergent Kinetic Resolution of 1,5-Enynes.

Authors:  Patrick T Bohan; F Dean Toste
Journal:  J Am Chem Soc       Date:  2017-08-03       Impact factor: 15.419

2.  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

3.  Rhodium-catalyzed intra- and intermolecular [5 + 2] cycloaddition of 3-acyloxy-1,4-enyne and alkyne with concomitant 1,2-acyloxy migration.

Authors:  Xing-Zhong Shu; Xiaoxun Li; Dongxu Shu; Suyu Huang; Casi M Schienebeck; Xin Zhou; Patrick J Robichaux; Weiping Tang
Journal:  J Am Chem Soc       Date:  2012-03-12       Impact factor: 15.419

4.  Cycloisomerization of dienes with carbophilic lewis acids: mimicking terpene biosynthesis with Pt(II) catalysts.

Authors:  William D Kerber; Michel R Gagné
Journal:  Org Lett       Date:  2005-07-21       Impact factor: 6.005

5.  Pt-catalyzed pentannulations from in situ generated metallo-carbenoids utilizing propargylic esters.

Authors:  B A Bhanu Prasad; Francis K Yoshimoto; Richmond Sarpong
Journal:  J Am Chem Soc       Date:  2005-09-14       Impact factor: 15.419

6.  Interception of a Rautenstrauch intermediate by alkynes for [5+2] cycloaddition: rhodium-catalyzed cycloisomerization of 3-acyloxy-4-ene-1,9-diynes to bicyclo[5.3.0]decatrienes.

Authors:  Xing-zhong Shu; Suyu Huang; Dongxu Shu; Ilia A Guzei; Weiping Tang
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-11       Impact factor: 15.336

7.  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

8.  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

Review 9.  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

10.  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
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