Literature DB >> 33078893

Assembly of Complex 1,4-Cycloheptadienes by (4+3) Cycloaddition of Rhodium(II) and Gold(I) Non-Acceptor Carbenes.

Helena Armengol-Relats1,2, Mauro Mato1,2, Antonio M Echavarren1,2.   

Abstract

The formal (4+3) cycloaddition of 1,3-dienes with Rh(II) and Au(I) non-acceptor vinyl carbenes, generated from vinylcycloheptatrienes or alkoxyenynes, respectively, leads to 1,4-cycloheptadienes featuring complex and diverse substitution patterns, including natural dyctiopterene C' and a hydroxylated derivative of carota-1,4-diene. A complete mechanistic picture is presented, in which Au(I) and Rh(II) non-acceptor vinyl carbenes were shown to undergo a vinylcyclopropanation/Cope rearrangement or a direct (4+3) cycloaddition that takes place in a non-concerted manner.
© 2020 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.

Entities:  

Keywords:  cycloadditions; cycloheptadienes; decarbenation reactions; enyne cycloisomerizations; metal carbenes

Year:  2020        PMID： 33078893      PMCID： PMC7894532          DOI： 10.1002/anie.202012092

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  42 in total

1.  Gold-catalyzed nucleophilic cyclization of functionalized allenes: a powerful access to carbo- and heterocycles.

Authors:  Norbert Krause; Christian Winter
Journal:  Chem Rev       Date:  2011-02-11       Impact factor: 60.622

2.  Cyclopropane-alkene metathesis by gold(i)-catalyzed decarbenation of persistent cyclopropanes.

Authors:  Mauro Mato; Inmaculada Martín-Torres; Bart Herlé; Antonio M Echavarren
Journal:  Org Biomol Chem       Date:  2019-04-24       Impact factor: 3.876

3.  Cyclopropanation with gold(I) carbenes by retro-Buchner reaction from cycloheptatrienes.

Authors:  César R Solorio-Alvarado; Yahui Wang; Antonio M Echavarren
Journal:  J Am Chem Soc       Date:  2011-07-20       Impact factor: 15.419

4.  Gold-catalyzed cycloisomerization of 1,6,8-dienyne carbonates and esters to cis-cyclohepta-4,8-diene-fused pyrrolidines.

Authors:  Weidong Rao; Stuart Neil Berry; Philip Wai Hong Chan
Journal:  Chemistry       Date:  2014-08-11       Impact factor: 5.236

5.  Ligand-controlled access to [4 + 2] and [4 + 3] cycloadditions in gold-catalyzed reactions of allene-dienes.

Authors:  Pablo Mauleón; Rachel M Zeldin; Ana Z González; F Dean Toste
Journal:  J Am Chem Soc       Date:  2009-05-13       Impact factor: 15.419

6.  Progress toward the total synthesis of (+/-)-actinophyllic acid.

Authors:  Rishi G Vaswani; Joshua J Day; John L Wood
Journal:  Org Lett       Date:  2009-10-15       Impact factor: 6.005

Review 7.  Recent progress on donor and donor-donor carbenes.

Authors:  Dong Zhu; Lianfen Chen; Hanlin Fan; Qinglin Yao; Shifa Zhu
Journal:  Chem Soc Rev       Date:  2020-02-10       Impact factor: 54.564

Review 8.  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

9.  Gold(I) as an artificial cyclase: short stereodivergent syntheses of (-)-epiglobulol and (-)-4β,7α- and (-)-4α,7α-aromadendranediols.

Authors:  Javier Carreras; Madeleine Livendahl; Paul R McGonigal; Antonio M Echavarren
Journal:  Angew Chem Int Ed Engl       Date:  2014-04-01       Impact factor: 15.336

10.  α,β-Unsaturated Gold(I) Carbenes by Tandem Cyclization and 1,5-Alkoxy Migration of 1,6-Enynes: Mechanisms and Applications.

Authors:  Pilar Calleja; Óscar Pablo; Beatrice Ranieri; Morgane Gaydou; Anthony Pitaval; María Moreno; Mihai Raducan; Antonio M Echavarren
Journal:  Chemistry       Date:  2016-08-16       Impact factor: 5.236
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  2 in total

1.  Assembly of Complex 1,4-Cycloheptadienes by (4+3) Cycloaddition of Rhodium(II) and Gold(I) Non-Acceptor Carbenes.

Authors:  Helena Armengol-Relats; Mauro Mato; Antonio M Echavarren
Journal:  Angew Chem Int Ed Engl       Date:  2020-11-24       Impact factor: 15.336

2.  Rh(II)-Catalyzed Alkynylcyclopropanation of Alkenes by Decarbenation of Alkynylcycloheptatrienes.

Authors:  Mauro Mato; Marc Montesinos-Magraner; Arnau R Sugranyes; Antonio M Echavarren
Journal:  J Am Chem Soc       Date:  2021-07-08       Impact factor: 15.419
  2 in total

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