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Tandem Conjugate Addition−Elimination for the Diastereoselective Synthesis of 4 E -Alkenyl syn -1,3-Diols

✍ Scribed by Rotulo-Sims, Delphine; Prunet, Joëlle


Book ID
127080023
Publisher
American Chemical Society
Year
2007
Tongue
English
Weight
79 KB
Volume
9
Category
Article
ISSN
1523-7060

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Synthesis of 4, 6-dialkyl-1,3-dioxins. V
✍ Raymond L Funk; Gary L Bolton 📂 Article 📅 1988 🏛 Elsevier Science 🌐 French ⚖ 271 KB

The title compounds 4 are prepared from 4-alkyldioxins 2 via a metalation, alkylation sequence. The dialkyl dioxins 4 are thermally labile (providing enones) and undergo highly stereoselective hydroboration or hydrogenation reactions to provide enti,anti-1,2,3-triols and syn-1,3-diols, respectively.