Literature DB >> 17173145

Ring closing enyne metathesis: a powerful tool for the synthesis of heterocycles.

Hélène Villar1, Marcus Frings, Carsten Bolm.   

Abstract

The ring closing metathesis (RCM) is a powerful method in organic synthesis for the preparation of cyclic compounds by formation of new carbon-carbon bonds. In the past years a particular subclass of the RCM, the ring closing enyne metathesis (RCEYM), has attracted attention due to its synthetic potential in the generation of ring structures with 1,3-diene moieties, which can subsequently be further functionalised. In this tutorial review mechanistic considerations will be described and the synthetic power of this useful and attractive carbon-carbon bond forming reaction will be illustrated by recent examples of RCEYM applications in the preparation of heterocyclic compounds.

Entities:  

Year:  2006        PMID: 17173145     DOI: 10.1039/b508899m

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  13 in total

1.  Palladium-catalyzed 1,1-difunctionalization of ethylene.

Authors:  Vaneet Saini; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2012-07-10       Impact factor: 15.419

2.  Synthesis of polycyclic benzofused nitrogen heterocycles via a tandem ynamide benzannulation/ring-closing metathesis strategy. Application in a formal total synthesis of (+)-FR900482.

Authors:  Xiao Yin Mak; Aimee L Crombie; Rick L Danheiser
Journal:  J Org Chem       Date:  2011-02-15       Impact factor: 4.354

3.  Endo-selective enyne ring-closing metathesis promoted by stereogenic-at-Mo monoalkoxide and monoaryloxide complexes. Efficient synthesis of cyclic dienes not accessible through reactions with Ru carbenes.

Authors:  Yeon-Ju Lee; Richard R Schrock; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2009-08-05       Impact factor: 15.419

4.  Ene-yne cross-metathesis with ruthenium carbene catalysts.

Authors:  Cédric Fischmeister; Christian Bruneau
Journal:  Beilstein J Org Chem       Date:  2011-02-04       Impact factor: 2.883

5.  Synthesis and biological evaluation of carbocyclic analogues of pachastrissamine.

Authors:  Yongseok Kwon; Jayoung Song; Hoon Bae; Woo-Jung Kim; Joo-Youn Lee; Geun-Hee Han; Sang Kook Lee; Sanghee Kim
Journal:  Mar Drugs       Date:  2015-02-03       Impact factor: 5.118

6.  Domino ring-opening-ring-closing enyne metathesis vs enyne metathesis of norbornene derivatives with alkynyl side chains. Construction of condensed polycarbocycles.

Authors:  Ritabrata Datta; Subrata Ghosh
Journal:  Beilstein J Org Chem       Date:  2018-10-25       Impact factor: 2.883

7.  Organic-inorganic hybrid silica material derived from a monosilylated Grubbs-Hoveyda ruthenium carbene as a recyclable metathesis catalyst.

Authors:  Guadalupe Borja; Roser Pleixats; Ramón Alibés; Xavier Cattoën; Michel Wong Chi Man
Journal:  Molecules       Date:  2010-08-23       Impact factor: 4.411

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.  Ruthenium-catalyzed intramolecular [2+2+2] cycloaddition and tandem cross-metathesis of triynes and enediynes.

Authors:  Wei Yuan; Yin Wei; Min Shi
Journal:  ChemistryOpen       Date:  2013-02-19       Impact factor: 2.911

10.  One-pot cross-enyne metathesis (CEYM)-Diels-Alder reaction of gem-difluoropropargylic alkynes.

Authors:  Santos Fustero; Paula Bello; Javier Miró; María Sánchez-Roselló; Günter Haufe; Carlos Del Pozo
Journal:  Beilstein J Org Chem       Date:  2013-11-28       Impact factor: 2.883

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