Efficient synthesis of substituted vinyl ethers using the Julia olefination.
Julia olefination between alpha-alkoxy sulfones 2a-c and a wide variety of ketones or aldehydes afforded substituted vinyl ethers in 46-90% yields. Sulfones 2a-c were readily prepared in two steps from commercially available reagents in 68-80% yields. Optimization revealed that the nature of the base, the solvent, and the temperature were crucial to obtaining the desired vinyl ethers. [reaction: see text]
Surprenant
Simon
S
Department of Medicinal Chemistry, Merck Frosst Centre for Therapeutic Research, P.O. Box 1005, Pointe-Claire/Dorval, Québec, Canada, H9R 4P8.
Chan
Wing Yan
WY
Berthelette
Carl
C