Organic Letters 2003-12-11

Efficient synthesis of substituted vinyl ethers using the Julia olefination.

Simon Surprenant, Wing Yan Chan, Carl Berthelette

Index: Org. Lett. 5 , 4851, (2003)

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Abstract

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]