Synthesis 2010(15): 2497-2511  
DOI: 10.1055/s-0030-1258166
REVIEW
© Georg Thieme Verlag Stuttgart ˙ New York

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;
Further Information

Publication History

Received 31 March 2010
Publication Date:
12 July 2010 (online)

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

61

Unpublished results from this laboratory.

71

Initial report using sodium methoxide: Ref. 69b.