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Synthesis 2003(1): 0001-0018
DOI: 10.1055/s-2003-36243
DOI: 10.1055/s-2003-36243
REVIEW
© Georg Thieme Verlag Stuttgart · New York
Enyne Metathesis Catalyzed by Ruthenium Carbene Complexes
Further Information
Received
28 October 2002
Publication Date:
18 December 2002 (online)
Publication History
Publication Date:
18 December 2002 (online)
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.
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1 Introduction
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2 Catalysts and Mechanism
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3 Ring-Closing Enyne Metathesis
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3.1 Metathesis of Substituted Enynes and the Influence of an Ethylene Atmosphere
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3.2 Formation of Different Ring-Sizes
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3.3 Tandem Metathesis Reactions
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3.4 Tandem Metathesis - Cycloaddition Reactions
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3.5 Metathesis of Carbohydrate-Derived Enynes
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3.6 Metathesis of Amino Acid- and β-Lactam-Derived Enynes
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3.7 Enyne Metathesis in Natural Product Syntheses
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4 Cross Enyne Metathesis
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4.1 Metathesis with Substituted Alkynes and Ethylene Gas
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4.2 Metathesis with Substituted Alkynes and Alkenes
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5 Concluding Remarks
Key words
alkenes - alkynes - carbene complexes - catalysis - Diels-Alder reactions - enynes - metathesis - ring closure - ruthenium - tandem reactions
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