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Literature DB >> 15355093

AuCl(3)-catalyzed synthesis of highly substituted furans from 2-(1-alkynyl)-2-alken-1-ones.

Tuanli Yao¹, Xiaoxia Zhang, Richard C Larock.

Abstract

Highly substituted furans have been synthesized by the reaction of 2-(1-alkynyl)-2-alken-1-ones and various nucleophiles under very mild reaction conditions in good to excellent yields. Gold and some other transition metals are efficient catalysts for this reaction.

Entities: Chemical

Year: 2004 PMID： 15355093 DOI： 10.1021/ja0466964

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

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Cited

27 in total

1. Pt-catalyzed cyclization/migration of propargylic alcohols for the synthesis of 3(2H)-furanones, pyrrolones, indolizines, and indolizinones.

Authors: Eric M Bunnelle; Cameron R Smith; Sharon K Lee; Surendra W Singaram; Allison J Rhodes; Richmond Sarpong
Journal: Tetrahedron Date: 2008-02-28 Impact factor: 2.457

2. Gold-catalyzed 1,2-migration of silicon, tin, and germanium en route to C-2 substituted fused pyrrole-containing heterocycles.

Authors: Ilya V Seregin; Vladimir Gevorgyan
Journal: J Am Chem Soc Date: 2006-09-20 Impact factor: 15.419

3. 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

AuCl(3)-catalyzed synthesis of highly substituted furans from 2-(1-alkynyl)-2-alken-1-ones.

1. Pt-catalyzed cyclization/migration of propargylic alcohols for the synthesis of 3(2H)-furanones, pyrrolones, indolizines, and indolizinones.

2. Gold-catalyzed 1,2-migration of silicon, tin, and germanium en route to C-2 substituted fused pyrrole-containing heterocycles.

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

4. Recent Advances in Transition Metal-Catalyzed Glycosylation.

Review 5. Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

6. Mechanism of AuCl₃-catalyzed cyclization of 1-(indol-2-yl)-3-alkyn-1-ols: a DFT study.

7. 1,2-Halogen migration in haloallenyl ketones: regiodivergent synthesis of halofurans.

8. Solution-phase synthesis of a highly substituted furan library.

9. Multisubstituted N-fused heterocycles via transition metal-catalyzed cycloisomerization protocols.

10. Synthesis of 3,4-disubstituted 2H-benzopyrans through C-C bond formation via electrophilic cyclization.