Literature DB >> 11777444

Efficient synthesis of 2-mono- and 2,5-disubstituted furans via the CuI-catalyzed cycloisomerization of alkynyl ketones.

Alexander V Kel'in1, Vladimir Gevorgyan.   

Abstract

A mild, general, and efficient method for the synthesis of 2-monosubstituted and 2,5-disubstituted furans via the CuI-catalyzed cycloisomerization of alkynyl ketones was developed. It was demonstrated that furans containing both acid- and base-labile groups could be easily synthesized using this methodology. A plausible mechanism for this transformation is proposed.

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Year:  2002        PMID： 11777444     DOI： 10.1021/jo010832v

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  21 in total

1.  Double cycloisomerization as a novel and expeditious route to tricyclic heteroaromatic compounds: short and highly diastereoselective synthesis of (+/-)-tetraponerine T6.

Authors:  Joseph T Kim; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2002-12-26       Impact factor: 6.005

2.  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

3.  A novel 1,2-migration of acyloxy, phosphatyloxy, and sulfonyloxy groups in allenes: efficient synthesis of tri- and tetrasubstituted furans.

Authors:  Anna W Sromek; Alexander V Kel'in; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2004-04-19       Impact factor: 15.336

4.  Acid-promoted cyclization reactions of tetrahydroindolinones. Model studies for possible application in a synthesis of selaginoidine.

Authors:  Mickea D Rose; Michael P Cassidy; Paitoon Rashatasakhon; Albert Padwa
Journal:  J Org Chem       Date:  2007-01-19       Impact factor: 4.354

5.  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 6.  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

7.  Bifunctional Phosphine Ligand Enabled Gold-Catalyzed Alkynamide Cycloisomerization: Access to Electron-Rich 2-Aminofurans and Their Diels-Alder Adducts.

Authors:  Xingguang Li; Xu Ma; Zhixun Wang; Pei-Nian Liu; Liming Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2019-10-15       Impact factor: 15.336

8.  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

9.  Selective partial reduction of various heteroaromatic compounds with bridgehead nitrogen via Birch reduction protocol.

Authors:  Joseph T Kim; Vladimir Gevorgyan
Journal:  J Org Chem       Date:  2005-03-18       Impact factor: 4.354

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

Authors:  Ilya V Seregin; Alex W Schammel; Vladimir Gevorgyan
Journal:  Tetrahedron       Date:  2008-07-14       Impact factor: 2.457
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