ChemInform Abstract: Synthesis via Vinyl Sulfones. Part 78. Synthesis of 6-Carbon Termini-Differentiated Stereotriads via Symchiral 2-Trifloxy-1,3-cyclohexadiene Monoepoxide.

✍ Scribed by Murphy Hentemann; P. L. Fuchs

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 34 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199927093

✦ Synopsis

Synthesis via Vinyl Sulfones.

Part 78. Synthesis of 6-Carbon Termini-Differentiated Stereotriads via Symchiral 2-Trifloxy-1,3cyclohexadiene Monoepoxide.

-Chiral epoxides such as (I) are investigated as precursors for the synthesis of functionalized derivatives. Thus, Stille coupling under optimized conditions gives products (III) in high selectivity together with small amounts of ketones (IV). Furthermore, reaction with nucleophiles proceeds mainly in the 1,4-addition mode to yield (VI) completely diastereoselectively. The usefulness of this reaction is demonstrated by the synthesis of the 6-carbon termini-differentiated ester aldehyde (XIV). -