Enyne Metathesis Catalyzed by Ruthenium Carbene Complexes

Carina Storm Poulsen; Robert Madsen

doi:10.1055/s-2003-36243

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Synthesis 2003(1): 0001-0018
DOI: 10.1055/s-2003-36243

REVIEW

Enyne Metathesis Catalyzed by Ruthenium Carbene Complexes

Carina Storm Poulsen, Robert Madsen*
Department of Chemistry, Building 201, Technical University of Denmark, 2800 Lyngby, Denmark
Fax: +4545933968; e-Mail: rm@kemi.dtu.dk;

Further Information

Publication History

Received 28 October 2002
Publication Date:
18 December 2002 (online)

Abstract
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Abstract

Enyne metathesis combines an alkene and an alkyne into a 1,3-diene. The first enyne metathesis reaction catalyzed by a ruthenium carbene complex was reported in 1994. This review covers the advances in this transformation during the last eight years with particular emphasis on methodology development and synthetic applications.

1 Introduction
2 Catalysts and Mechanism
3 Ring-Closing Enyne Metathesis
3.1 Metathesis of Substituted Enynes and the Influence of an Ethylene Atmosphere
3.2 Formation of Different Ring-Sizes
3.3 Tandem Metathesis Reactions
3.4 Tandem Metathesis - Cycloaddition Reactions
3.5 Metathesis of Carbohydrate-Derived Enynes
3.6 Metathesis of Amino Acid- and β-Lactam-Derived Enynes
3.7 Enyne Metathesis in Natural Product Syntheses
4 Cross Enyne Metathesis
4.1 Metathesis with Substituted Alkynes and Ethylene Gas
4.2 Metathesis with Substituted Alkynes and Alkenes
5 Concluding Remarks

Key words

alkenes - alkynes - carbene complexes - catalysis - Diels-Alder reactions - enynes - metathesis - ring closure - ruthenium - tandem reactions

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