Literature DB >> 20352055

Gold-catalyzed Intermolecular [4C + 3C] Cycloaddition Reactions.

Benjamin W Gung1, Lauren N Bailey, Josh Wonser.   

Abstract

In the presence of the N-heterocyclic carbene gold catalyst (NHC-AuIPr, 7), propargyl esters 1a-f and 13 undergo a [4C + 3C] cycloaddition reaction with cyclopentadiene and furan under mild conditions. The evidence suggests the formation of the seven-membered ring occurs by a direct cycloaddition process, rather than a stepwise cyclopropanation/Cope rearrangement sequence.

Entities:  

Year:  2010        PMID： 20352055      PMCID： PMC2844647          DOI： 10.1016/j.tetlet.2010.02.099

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  23 in total

1.  Platinum-catalyzed intramolecular [4C+3C] cycloaddition between dienes and allenes.

Authors:  Beatriz Trillo; Fernando López; Moisés Gulías; Luis Castedo; José L Mascareñas
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

2.  Cortistatins A, B, C, and D, anti-angiogenic steroidal alkaloids, from the marine sponge Corticium simplex.

Authors:  Shunji Aoki; Yasuo Watanabe; Mami Sanagawa; Andi Setiawan; Naoyuki Kotoku; Motomasa Kobayashi
Journal:  J Am Chem Soc       Date:  2006-03-15       Impact factor: 15.419

3.  Gold(I)-catalyzed stereoselective olefin cyclopropanation.

Authors:  Magnus J Johansson; David J Gorin; Steven T Staben; F Dean Toste
Journal:  J Am Chem Soc       Date:  2005-12-28       Impact factor: 15.419

4.  On the nature of the reactive intermediates in gold-catalyzed cycloisomerization reactions.

Authors:  Alois Fürstner; Louis Morency
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

5.  Ru-catalyzed ring-opening and substitution reactions of heteroaromatic compounds using propargylic carboxylates as precursors of vinylcarbenoids.

Authors:  Koji Miki; Michinobu Fujita; Sakae Uemura; Kouichi Ohe
Journal:  Org Lett       Date:  2006-04-13       Impact factor: 6.005

6.  Gold-catalyzed [4C+2C] cycloadditions of allenedienes, including an enantioselective version with new phosphoramidite-based catalysts: mechanistic aspects of the divergence between [4C+3C] and [4C+2C] pathways.

Authors:  Isaac Alonso; Beatriz Trillo; Fernando López; Sergi Montserrat; Gregori Ujaque; Luis Castedo; Agustí Lledós; Jose L Mascareñas
Journal:  J Am Chem Soc       Date:  2009-09-16       Impact factor: 15.419

7.  On the impact of steric and electronic properties of ligands on gold(I)-catalyzed cycloaddition reactions.

Authors:  Diego Benitez; Ekaterina Tkatchouk; Ana Z Gonzalez; William A Goddard; F Dean Toste
Journal:  Org Lett       Date:  2009-11-05       Impact factor: 6.005

8.  Ruthenium-catalyzed cyclopropanation of alkenes using propargylic carboxylates as precursors of vinylcarbenoids.

Authors:  Koji Miki; Kouichi Ohe; Sakae Uemura
Journal:  J Org Chem       Date:  2003-10-31       Impact factor: 4.354

9.  Asymmetric [4+3] cycloadditions between benzofuranyldiazoacetates and dienes: formal synthesis of (+)-frondosin B.

Authors:  Jeremy P Olson; Huw M L Davies
Journal:  Org Lett       Date:  2008-01-24       Impact factor: 6.005

10.  The first transannular [4+3] cycloaddition reaction: synthesis of the ABCD ring structure of cortistatins.

Authors:  Derek T Craft; Benjamin W Gung
Journal:  Tetrahedron Lett       Date:  2008-10-06       Impact factor: 2.415
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  4 in total

Review 1.  Rhodium-catalyzed acyloxy migration of propargylic esters in cycloadditions, inspiration from the recent "gold rush".

Authors:  Xing-Zhong Shu; Dongxu Shu; Casi M Schienebeck; Weiping Tang
Journal:  Chem Soc Rev       Date:  2012-12-07       Impact factor: 54.564

2.  Rhodium- and platinum-catalyzed [4+3] cycloaddition with concomitant indole annulation: synthesis of cyclohepta[b]indoles.

Authors:  Dongxu Shu; Wangze Song; Xiaoxun Li; Weiping Tang
Journal:  Angew Chem Int Ed Engl       Date:  2013-02-10       Impact factor: 15.336

Review 3.  Gold(I)-catalyzed enantioselective cycloaddition reactions.

Authors:  Fernando López; José L Mascareñas
Journal:  Beilstein J Org Chem       Date:  2013-10-30       Impact factor: 2.883

Review 4.  Recent applications of the divinylcyclopropane-cycloheptadiene rearrangement in organic synthesis.

Authors:  Sebastian Krüger; Tanja Gaich
Journal:  Beilstein J Org Chem       Date:  2014-01-16       Impact factor: 2.883
  4 in total

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