Literature DB >> 15761893

Electrophilic activation and cycloisomerization of enynes: a new route to functional cyclopropanes.

Christian Bruneau1.   

Abstract

Transformations of enynes in the presence of transition-metal catalysts have played an important role in the preparation of a variety of cyclic compounds. Recent developments in the activation of triple carbon-carbon bonds by electrophilic metal centers have provided a new entry to the selective synthesis of cyclopropane derivatives from enynes. The mechanisms of these reactions involve catalytic species with both ionic and cyclopropylcarbenoid character. This type of activation will undoubtedly be further developed for application to other unsaturated hydrocarbons and inspire new catalytic cascade reaction sequences. This Minireview discusses the recent developments in electrophilic activation of enynes and shows that simple catalysts such as [Ru(3)(CO)(12)], PtCl(2), and cationic gold complexes are efficient precursors to promote the formation of functional polyclic compounds.

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Year:  2005        PMID: 15761893     DOI: 10.1002/anie.200462568

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


  10 in total

1.  Synthesis of acyclic alpha,beta-unsaturated ketones via Pd(II)-catalyzed intermolecular reaction of alkynamides and alkenes.

Authors:  Norie Momiyama; Matthew W Kanan; David R Liu
Journal:  J Am Chem Soc       Date:  2007-02-06       Impact factor: 15.419

2.  Computational Studies on the Pt(II)-Catalyzed Cycloisomerization of 1,6-dienes into Bicyclopropanes: A Mechanistic Quandary Evaluated by DFT.

Authors:  Franziska Bell; Jason Holland; Jennifer C Green; Michel R Gagné
Journal:  Organometallics       Date:  2009-04-13       Impact factor: 3.876

Review 3.  Ligand effects in homogeneous Au catalysis.

Authors:  David J Gorin; Benjamin D Sherry; F Dean Toste
Journal:  Chem Rev       Date:  2008-07-25       Impact factor: 60.622

4.  Asymmetric Au-catalyzed cycloisomerization of 1,6-enynes: An entry to bicyclo[4.1.0]heptene.

Authors:  Alexandre Pradal; Chung-Meng Chao; Patrick Y Toullec; Véronique Michelet
Journal:  Beilstein J Org Chem       Date:  2011-07-26       Impact factor: 2.883

5.  Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity.

Authors:  Ruth Dorel; Antonio M Echavarren
Journal:  Chem Rev       Date:  2015-04-06       Impact factor: 60.622

6.  Gold-Catalyzed Intramolecular Cyclizations of Cyclopropenes with Propargylic Esters.

Authors:  Peng-Long Zhu; Xiang-Ying Tang; Min Shi
Journal:  ChemistryOpen       Date:  2015-10-12       Impact factor: 2.911

7.  Unpredictable cycloisomerization of 1,11-dien-6-ynes by a common cobalt catalyst.

Authors:  Abdusalom A Suleymanov; Dmitry V Vasilyev; Valentin V Novikov; Yulia V Nelyubina; Dmitry S Perekalin
Journal:  Beilstein J Org Chem       Date:  2017-03-31       Impact factor: 2.883

8.  Divergent reaction pathways in gold-catalyzed cycloisomerization of 1,5-enynes containing a cyclopropane ring: dramatic ortho substituent and temperature effects.

Authors:  Gen-Qiang Chen; Wei Fang; Yin Wei; Xiang-Ying Tang; Min Shi
Journal:  Chem Sci       Date:  2016-03-04       Impact factor: 9.825

9.  Au-catalyzed skeletal rearrangement of O-propargylic oximes via N-O bond cleavage with the aid of a Brønsted base cocatalyst.

Authors:  Keigo Shiga; Ilya D Gridnev; Masahiro Terada; Itaru Nakamura
Journal:  Chem Sci       Date:  2019-04-18       Impact factor: 9.825

10.  A rhodium catalyzed cycloisomerization and tandem Diels-Alder reaction for facile access to diverse bicyclic and tricyclic heterocycles.

Authors:  Yirong Zhou; Ali Nikbakht; Felix Bauer; Bernhard Breit
Journal:  Chem Sci       Date:  2019-04-03       Impact factor: 9.825

  10 in total

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