Literature DB >> 28239480

C-C Bond Migration in the Cycloisomerization of 1,6-Enynes.

Susan M Stevenson1, Eric T Newcomb2, Eric M Ferreira1.   

Abstract

A full account of our investigation of C-C bond migration in the cycloisomerization of oxygen-tethered 1,6-enynes is described. Under Pt(II) and/or Ir(I) catalysis, cyclic and acylic alkyl groups were found to undergo 1,2-shifts into metal carbenoid intermediates. Interestingly, this process does not appear to be driven by the release of ring strain, and thus provides access to large carbocyclic frameworks. The beneficial effect of CO on the Pt(II) and Ir(I) catalytic systems is also evaluated.

Entities:  

Year:  2016        PMID： 28239480      PMCID： PMC5321652          DOI： 10.1039/C6QO00224B

Source DB:  PubMed          Journal:  Org Chem Front        ISSN： 2052-4110            Impact factor:   5.281


  44 in total

1.  The mechanistic puzzle of transition-metal-catalyzed skeletal rearrangements of enynes.

Authors:  Cristina Nieto-Oberhuber; Salomé López; Eloísa Jiménez-Núñez; Antonio M Echavarren
Journal:  Chemistry       Date:  2006-08-07       Impact factor: 5.236

Review 2.  Gold-catalyzed cycloisomerizations of enynes: a mechanistic perspective.

Authors:  Eloísa Jiménez-Núñez; Antonio M Echavarren
Journal:  Chem Rev       Date:  2008-07-18       Impact factor: 60.622

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Review 4.  The exploration of macrocycles for drug discovery--an underexploited structural class.

Authors:  Edward M Driggers; Stephen P Hale; Jinbo Lee; Nicholas K Terrett
Journal:  Nat Rev Drug Discov       Date:  2008-07       Impact factor: 84.694

5.  Total Synthesis of Gelsenicine via a Catalyzed Cycloisomerization Strategy.

Authors:  Eric T Newcomb; Phil C Knutson; Blaine A Pedersen; Eric M Ferreira
Journal:  J Am Chem Soc       Date:  2015-12-30       Impact factor: 15.419

6.  Cyclobutenes by platinum-catalyzed cycloisomerization reactions of enynes.

Authors:  Alois Fürstner; Paul W Davies; Tobias Gress
Journal:  J Am Chem Soc       Date:  2005-06-15       Impact factor: 15.419

7.  New annulations via platinum-catalyzed enyne cyclization and cyclopropane cleavage.

Authors:  Cristina Nevado; Catalina Ferrer; Antonio M Echavarren
Journal:  Org Lett       Date:  2004-09-02       Impact factor: 6.005

8.  Cycloisomerization of 1,n-enynes: challenging metal-catalyzed rearrangements and mechanistic insights.

Authors:  Véronique Michelet; Patrick Y Toullec; Jean-Pierre Genêt
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

9.  Gold vinylidene complexes: intermolecular C(sp3)-H insertions and cyclopropanations pathways.

Authors:  A Stephen K Hashmi; Marcel Wieteck; Ingo Braun; Matthias Rudolph; Frank Rominger
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-17       Impact factor: 15.336

10.  Atropisomeric [(diphosphine)Au2 Cl2 ] complexes and their catalytic activity towards asymmetric cycloisomerisation of 1,6-enynes.

Authors:  Elena M Barreiro; Ekaterina V Boltukhina; Andrew J P White; King Kuok Mimi Hii
Journal:  Chemistry       Date:  2014-12-11       Impact factor: 5.236
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  1 in total

1.  Iron-Catalyzed Cycloisomerization and C-C Bond Activation to Access Non-canonical Tricyclic Cyclobutanes.

Authors:  Frederik Kramm; Franziska Ullwer; Benedict Klinnert; Min Zheng; Bernd Plietker
Journal:  Angew Chem Int Ed Engl       Date:  2022-08-08       Impact factor: 16.823
  1 in total

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