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Synthesis of 3-alkylidene-piperidin-4-ones via one-pot cascade transylidation–olefination

✍ Scribed by Bing Wang

Publisher
Elsevier Science
Year
2009
Tongue
French
Weight
290 KB
Volume
50
Category
Article
ISSN
0040-4039

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✦ Synopsis

3-Alkylidene-piperidin-4-ones with diverse C-5 substitution patterns are synthesized via a one-pot cascade transylidation-olefination sequence. Tributylphosphorus ylides show distinct higher reactivity as compared to triphenyl analogs. t-Butanol is the solvent of choice for transylidation, while the Wittig olefination of aliphatic aldehydes requires MeCN as the solvent.

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✍ Ahlem Chamakh; Hassen Amri 📂 Article 📅 1998 🏛 Elsevier Science 🌐 French ⚖ 210 KB

A one pot synthesis of (E)-4-alkylidene-2-cyclohexen-l-ones 2 via a cross coupling of 2-( l-acetoxy alkyl) enones 1 and aliphatic 1,3-diketones in the presence of anhydrous potassium carbonate in absolute ethanol at reflux, is reported.