Methods for Vinyl Ether Synthesis

David J. Winternheimer; Ryan E. Shade; Craig A. Merlic

doi:10.1055/s-0030-1258166

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Synthesis 2010(15): 2497-2511
DOI: 10.1055/s-0030-1258166

REVIEW

Methods for Vinyl Ether Synthesis

David J. Winternheimer, Ryan E. Shade, Craig A. Merlic*
Department of Chemistry and Biochemistry, University of California, Los Angeles, 607 Charles E. Young Drive, Los Angeles, CA 90095-1569, USA
Fax: +1(310)2063722; e-Mail: Merlic@chem.ucla.edu;

Weitere Informationen

Publikationsverlauf

Received 31 March 2010
Publikationsdatum:
12. Juli 2010 (online)

Abstract
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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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