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Cycloadditions of 2-aza-1,3-dienes to aldehydes: a Diels-Alder strategy for the diastereoselective hydroxyalkylation of carboxylic acid derivatives

✍ Scribed by Deogratias Ntirampebura; Léon Ghosez

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
197 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

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-hydroxyamides 4.

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The 2π + 2π cycloaddition of an allyl cation to (1Z,3E)-cycloalkadienes. Evidence for a stepwise process in the lonic Diels-Alder reaction.
✍ Paul G. Gassman; Subhash P. Chavan; Lawrence B. Fertel 📂 Article 📅 1990 🏛 Elsevier Science 🌐 French ⚖ 261 KB

Treatment of (lZ,3E)-cycloalkadienes with 2-vinyl-1,3-dioxolane under acidic conditions produced 1:l cycloadducts in which an intermediate ally1 cation added to the dienes to give tram-fused cyclobutanes as the major products.