Abstract
Deceptively simple as the structure may appear, there is no single
general method by which to synthesize the vinyl (enol) ether functionality.
However, there exists a diverse array of complementary methods by
which this functionality has been achieved. This review presents
the scope and limitations of these methods according to reaction
type, specifically via ether modifications, elimination reactions,
carbonyl olefinations, alcohol additions and carbon-oxygen
coupling reactions.
1 Introduction
2 Modification of Ethers
2.1 Vinyl Ether Substrates
2.2 Allyl Ether Substrates
2.3 Acetylenic Ether Substrates
3 Elimination Reactions
3.1 Halide and Pseudohalide Leaving Groups
3.2 Alkoxide and Silyloxide Leaving Groups
3.3 Selenium Oxidation-Elimination
4 Olefination of Carbonyl Substrates
4.1 Phosphorus Reagents
4.2 Silicon Reagents
4.3 Sulfur Reagents
4.4 Metal Carbene Reagents
5 Addition of Alcohols
5.1 Alkyne Substrates
5.2 Dicarbonyl Substrates
6 Carbon-Oxygen Coupling Reactions
6.1 Palladium-Mediated Reactions
6.2 Copper-Mediated Reactions
7 Conclusion
Key words
alkenation - alkenes - enols - ethers - olefination
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