Literature DB >> 16906747

Search for solutions to the reactivity and selectivity problems in enyne metathesis.

Eric C Hansen1, Daesung Lee.   

Abstract

Enyne metathesis is a powerful carbon-carbon bond-forming reaction to generate 1,3-dienes from an alkyne and an alkene. Different from the diene and diyne metathesis, the enyne metathesis suffers from both regio- and stereoselectivity problems, yet there is no general solution to these problems. This Account briefly describes the evolution of various new strategies and substrate platforms from these laboratories to address the reactivity and selectivity issues in the enyne metathesis processes.

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Year:  2006        PMID: 16906747     DOI: 10.1021/ar050024g

Source DB:  PubMed          Journal:  Acc Chem Res        ISSN: 0001-4842            Impact factor:   22.384


  12 in total

1.  Reverse cope elimination of hydroxylamines and alkenes or alkynes: theoretical investigation of tether length and substituent effects.

Authors:  Elizabeth H Krenske; Edwin C Davison; Ian T Forbes; Jacqueline A Warner; Adrian L Smith; Andrew B Holmes; K N Houk
Journal:  J Am Chem Soc       Date:  2012-01-17       Impact factor: 15.419

2.  Stereochemical and skeletal diversity arising from amino propargylic alcohols.

Authors:  Daniela Pizzirani; Taner Kaya; Paul A Clemons; Stuart L Schreiber
Journal:  Org Lett       Date:  2010-06-18       Impact factor: 6.005

3.  Total synthesis of (3R,9R,10R)-panaxytriol via tandem metathesis and metallotropic [1,3]-shift as a key step.

Authors:  Eun Jin Cho; Daesung Lee
Journal:  Org Lett       Date:  2007-12-13       Impact factor: 6.005

4.  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

5.  Absence of the Thorpe-Ingold Effect by gem-Diphenyl Groups in Ring-Closing Enyne Metathesis.

Authors:  Yi Jin Kim; Jonathan B Grimm; Daesung Lee
Journal:  Tetrahedron Lett       Date:  2007-11-05       Impact factor: 2.415

6.  A Simple Procedure for the Synthesis of β-Hydroxyallenamides via Homoallenylation of Aldehydes.

Authors:  Byeong-Seon Kim; Osvaldo Gutierrez; Marisa C Kozlowski; Patrick J Walsh
Journal:  Adv Synth Catal       Date:  2018-01-30       Impact factor: 5.837

7.  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

8.  Tandem cross enyne metathesis (CEYM)-intramolecular Diels-Alder reaction (IMDAR). An easy entry to linear bicyclic scaffolds.

Authors:  Javier Miró; María Sánchez-Roselló; Álvaro Sanz; Fernando Rabasa; Carlos Del Pozo; Santos Fustero
Journal:  Beilstein J Org Chem       Date:  2015-08-25       Impact factor: 2.883

9.  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

10.  Stereoselective synthesis of pentasubstituted 1,3-dienes via Ni-catalyzed reductive coupling of unsymmetrical internal alkynes.

Authors:  Zhijun Zhou; Jiachang Chen; Herong Chen; Wangqing Kong
Journal:  Chem Sci       Date:  2020-09-10       Impact factor: 9.825

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