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Literature DB >> 19425591

Counterion effects in a gold-catalyzed synthesis of pyrroles from alkynyl aziridines.

Abstract

Aryl-substituted N-tosyl alkynyl aziridines undergo a gold-catalyzed ring expansion to afford 2,5-substituted pyrrole products. Under certain conditions, a ring-expansion and rearrangement leads to 2,4-substituted pyrroles. The reaction pathway is determined by the counterion to the gold catalyst.

Entities: Chemical

Year: 2009 PMID： 19425591 DOI： 10.1021/ol900609f

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

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Cited

13 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. Computation-guided development of Au-catalyzed cycloisomerizations proceeding via 1,2-Si or 1,2-H migrations: regiodivergent synthesis of silylfurans.

Authors: Alexander S Dudnik; Yuanzhi Xia; Yahong Li; Vladimir Gevorgyan
Journal: J Am Chem Soc Date: 2010-06-09 Impact factor: 15.419

Review 3. 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

4. On the validity of Au-vinylidenes in the gold-catalyzed 1,2-migratory cycloisomerization of skipped propargylpyridines.

Authors: Yuanzhi Xia; Alexander S Dudnik; Yahong Li; Vladimir Gevorgyan
Journal: Org Lett Date: 2010-11-11 Impact factor: 6.005

Counterion effects in a gold-catalyzed synthesis of pyrroles from alkynyl aziridines.

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

2. Computation-guided development of Au-catalyzed cycloisomerizations proceeding via 1,2-Si or 1,2-H migrations: regiodivergent synthesis of silylfurans.

Review 3. Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

4. On the validity of Au-vinylidenes in the gold-catalyzed 1,2-migratory cycloisomerization of skipped propargylpyridines.

5. Solvent- and ligand-induced switch of selectivity in gold(I)-catalyzed tandem reactions of 3-propargylindoles.

6. Isotopic labelling studies for a gold-catalysed skeletal rearrangement of alkynyl aziridines.

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

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

9. Anatomy of gold catalysts: facts and myths.

10. 1,2-boryl migration empowers regiodivergent synthesis of borylated furans.