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Literature DB >> 16448102

Efficient synthesis of cyclopentenones from enynyl acetates via tandem Au(I)-catalyzed 3,3-rearrangement and the Nazarov reaction.

Abstract

A highly efficient method for the synthesis of versatile cyclopentenones from readily available enynyl acetates via tandem Au(I)-catalyzed 3,3-rearrangement and the Nazarov reaction is developed. Significant substrate flexibility and excellent control of the double bond position in the cyclopentenone ring render this an attractive method for cyclopentenone synthesis.

Entities: Chemical

Year: 2006 PMID： 16448102 DOI： 10.1021/ja057327q

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

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Cited

37 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. Using Nazarov electrocyclization to stage chemoselective [1,2]-migrations: stereoselective synthesis of functionalized cyclopentenones.

Authors: David Lebœuf; Jie Huang; Vincent Gandon; Alison J Frontier
Journal: Angew Chem Int Ed Engl Date: 2011-09-26 Impact factor: 15.336

3. 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

Efficient synthesis of cyclopentenones from enynyl acetates via tandem Au(I)-catalyzed 3,3-rearrangement and the Nazarov reaction.

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

2. Using Nazarov electrocyclization to stage chemoselective [1,2]-migrations: stereoselective synthesis of functionalized cyclopentenones.

3. 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.

4. Enantiomeric impurities in chiral synthons, catalysts, and auxiliaries. Part 3.

5. Synthesis and Applications of Hajos-Parrish Ketone Isomers.

6. Experimental and theoretical studies on the Nazarov cyclization/Wagner-Meerwein rearrangement sequence.

Review 7. Toward a symphony of reactivity: cascades involving catalysis and sigmatropic rearrangements.

8. Gold(I)-catalyzed enantioselective carboalkoxylation of alkynes.

Review 9. Metal-catalyzed double migratory cascade reactions of propargylic esters and phosphates.

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