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Asymmetric Diels–Alder Cycloaddition of 1-Aminocyclohexadiene to Chiral Acrylate: Synthesis of Enantiopure Bridgehead-Aminobicyclo[2.2.2]octane-2-carboxylic Acid Derivatives

✍ Scribed by Olivier Songis; Claude Didierjean; Camille Laurent; Jean Martinez; Monique Calmès


Publisher
John Wiley and Sons
Year
2007
Tongue
English
Weight
149 KB
Volume
2007
Category
Article
ISSN
1434-193X

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Cycloadditions of 2-aza-1,3-dienes to al
✍ Deogratias Ntirampebura; Léon Ghosez 📂 Article 📅 1999 🏛 Elsevier Science 🌐 French ⚖ 197 KB

2-Aza-1,3-dienes 1 which are readily prepared from carboxylic acids cycloadd to aldehydes to give good yields of 1,3-oxazinones 3. The cycloadditions were highly diastereoselective in favour of the endo adducts. Hydrolysis of 1,3-oxazinones 3 stereoselectively yielded the corresponding 13-hydroxyami