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Literature DB >> 18311994

Gold-catalyzed double migration-benzannulation cascade toward naphthalenes.

Alexander S Dudnik¹, Todd Schwier, Vladimir Gevorgyan.

Abstract

A novel gold(I)-catalyzed cycloisomerization of propargylic esters leading to unsymmetrically substituted naphthalenes has been developed. This cascade reaction involves an unprecedented tandem sequence of 1,3- and 1,2-migration of two different migrating groups. It is believed that this transformation likely proceeds via the formation of 1,3-diene intermediate or its precursor, which upon cyclization and aromatization steps transforms into the naphthalene core.

Entities: Chemical

Mesh：

Substances：

Year: 2008 PMID： 18311994 PMCID： PMC3679922 DOI： 10.1021/ol800229h

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

39 in total

1. Gold-catalyzed synthesis of substituted tetrahydronaphthalenes.

Authors: Christiane M Grisé; Louis Barriault
Journal: Org Lett Date: 2006-12-07 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. Metal-catalyzed [1,2]-alkyl shift in allenyl ketones: synthesis of multisubstituted furans.

Authors: Alexander S Dudnik; Vladimir Gevorgyan
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

5. 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

6. Gold catalysts: towards sustainable chemistry.

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

7. Synthesis of stable 2H-pyran-5-carboxylates via a catalyzed propargyl-Claisen rearrangement/oxa-6pi electrocyclization strategy.

Authors: Helge Menz; Stefan F Kirsch
Journal: Org Lett Date: 2006-10-12 Impact factor: 6.005

8. 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

9. 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

10. 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 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. 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

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

Gold-catalyzed double migration-benzannulation cascade toward naphthalenes.

1. Gold-catalyzed synthesis of substituted tetrahydronaphthalenes.

Review 2. Relativistic effects in homogeneous gold catalysis.

3. Gold-catalyzed organic reactions.

4. Metal-catalyzed [1,2]-alkyl shift in allenyl ketones: synthesis of multisubstituted furans.

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

6. Gold catalysts: towards sustainable chemistry.

7. Synthesis of stable 2H-pyran-5-carboxylates via a catalyzed propargyl-Claisen rearrangement/oxa-6pi electrocyclization strategy.

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

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

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

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

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

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

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

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

Review 6. Metal-catalyzed double migratory cascade reactions of propargylic esters and phosphates.

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

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

9. Recent advances in the gold-catalyzed additions to C-C multiple bonds.

10. Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity.