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Literature DB >> 17608434

Synthesis of functionalized pyrroles via gold(I)-catalyzed aza-Claisen-type rearrangement.

Abstract

Gold(I)-catalyzed cyclization of pentenynyl allyl tosylamides allows the rapid construction of functionalized pyrroles. The concerted aza-Claisen-type mechanism induces a complete selectivity of the process and allows the easy formation of quaternary centers.

Entities: Chemical

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Year: 2007 PMID： 17608434 DOI： 10.1021/ol0713032

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

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Cited

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

Review 2. 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

3. Synthesis of furans and pyrroles via migratory and double migratory cycloisomerization reactions of homopropargylic aldehydes and imines.

Authors: Roohollah Kazem Shiroodi; Claudia I Rivera Vera; Alexander S Dudnik; Vladimir Gevorgyan
Journal: Tetrahedron Lett Date: 2015-06-03 Impact factor: 2.415

4. 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

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

Synthesis of functionalized pyrroles via gold(I)-catalyzed aza-Claisen-type rearrangement.

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

Review 2. Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

3. Synthesis of furans and pyrroles via migratory and double migratory cycloisomerization reactions of homopropargylic aldehydes and imines.

4. A Reactivity-Driven Approach to the Discovery and Development of Gold-Catalyzed Organic Reactions.

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

Review 6. Ligand effects in homogeneous Au catalysis.

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

8. When gold can do what iodine cannot do: A critical comparison.

9. Intriguing mechanistic labyrinths in gold(I) catalysis.

10. Evidencing an inner-sphere mechanism for NHC-Au(I)-catalyzed carbene-transfer reactions from ethyl diazoacetate.