Literature DB >> 24501430

ORGANOCOPPER-MEDIATED TWO-COMPONENT SN2'-SUBSTITUTION CASCADE TOWARDS N-FUSED HETEROCYCLES.

D Chernyak1, V Gevorgyan1.   

Abstract

Organocuprates efficiently undergo reaction with heterocyclic propargyl mesylates at low temperature to produce N-fused heterocycles. The copper reagent plays a "double duty" in this cascade transformation, which proceeds through an SN2'-substitution followed by a consequent cycloisomerization step.

Entities:  

Keywords:  allenes; cycloisomerization; indolizines; propargyl mesylates; synthetic methods

Year:  2012        PMID： 24501430      PMCID： PMC3910007          DOI： 10.1007/s10593-012-0942-1

Source DB:  PubMed          Journal:  Chem Heterocycl Compd (N Y)        ISSN： 0009-3122            Impact factor:   1.277


  27 in total

1.  Enantioselective synthesis of and with allenes.

Authors:  Anja Hoffmann-Röder; Norbert Krause
Journal:  Angew Chem Int Ed Engl       Date:  2002-08-16       Impact factor: 15.336

Review 2.  Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes.

Authors:  Francisco Alonso; Irina P Beletskaya; Miguel Yus
Journal:  Chem Rev       Date:  2004-06       Impact factor: 60.622

3.  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

4.  Direct palladium-catalyzed alkynylation of N-fused heterocycles.

Authors:  Ilya V Seregin; Victoria Ryabova; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2007-06-01       Impact factor: 15.419

5.  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

6.  A novel Cu-assisted cycloisomerization of alkynyl imines: efficient synthesis of pyrroles and pyrrole-containing heterocycles.

Authors:  A V Kel'in; A W Sromek; V Gevorgyan
Journal:  J Am Chem Soc       Date:  2001-03-07       Impact factor: 15.419

7.  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

8.  Mechanistically diverse copper-, silver-, and gold-catalyzed acyloxy and phosphatyloxy migrations: efficient synthesis of heterocycles via cascade migration/cycloisomerization approach.

Authors:  Todd Schwier; Anna W Sromek; Dahrika M L Yap; Dmitri Chernyak; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2007-07-21       Impact factor: 15.419

9.  Lamellarin D bioconjugates I: Synthesis and cellular internalization of PEG-derivatives.

Authors:  Daniel Pla; Andrés Francesch; Pilar Calvo; Carmen Cuevas; Rosa Aligué; Fernando Albericio; Mercedes Alvarez
Journal:  Bioconjug Chem       Date:  2009-06       Impact factor: 4.774

10.  Pyrrolidine and piperidine formation via copper(II) carboxylate-promoted intramolecular carboamination of unactivated olefins: diastereoselectivity and mechanism.

Authors:  Eric S Sherman; Peter H Fuller; Dhanalakshmi Kasi; Sherry R Chemler
Journal:  J Org Chem       Date:  2007-04-12       Impact factor: 4.354
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