ChemInform Abstract: Stereochemistry of Lewis Acid and Fluoride Promoted Intramolecular Cyclization of β-(Alkoxycarbonyl)allylsilane with Enones. Synthesis of Bicyclo(4.3.0)nonanes.

✍ Scribed by C. KURODA; H. NOGAMI; Y. OHNISHI; Y. KIMURA; J. Y. SATOH

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 39 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199716066

✦ Synopsis

Stereochemistry of Lewis Acid and Fluoride Promoted Intramolecular

Cyclization of β-(Alkoxycarbonyl)allylsilane with Enones. Synthesis of Bicyclo(4.3.0)nonanes. -The title reaction is found to yield cyclohexanes and/or bicyclo(4.3.0) nonanes, a common unit present in terpenoid natural products. The stereochemistry depends on the geometry of the allylsilane used and gives essentially the same product distribution under Lewis acid and fluoride promotion, although the selectivity of the fluoride induced reaction is lower. Moreover, the selectivity is slightly higher for the (Z)-allylsilanes. -