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Electroreductive intramolecular coupling of γ- and δ-cyanoketones

✍ Scribed by Tatsuya Shono; Naoki Kise

Publisher
Elsevier Science
Year
1990
Tongue
French
Weight
245 KB
Volume
31
Category
Article
ISSN
0040-4039

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✦ Synopsis

Electroreduction of y-and 6-cyanoketones in i-PrOH gave cyclized products a-hydroxyketones and their dehydroxylated ketones, and this reaction was applied to the synthesis of dihydrojaswone, methyl dihydrojaswonate, and Rosaprostol. We have previously reported sowe unique electroreductive intramolecular coupling reactions of nonconjugated olefinic,* acety1enic.s and aromatic ketones' yielding cyclic tertiary alcohols. Recently, we have found that the electroreduction of sowe cyclic yand 6-cyanoketones 1 led to intramolecular coupling between carbonyl and cyano groups, and for-wed bicyclic a-hydroxyketones 2 and their dehydroxylated ketones 3 (eq.1).

📜 SIMILAR VOLUMES

Electroreductive intramolecular coupling
Electroreductive intramolecular coupling of aromatic δ- and ε-keto esters
✍ Naoki Kise; Kie Arimoto; Nasuo Ueda 📂 Article 📅 2003 🏛 Elsevier Science 🌐 French ⚖ 145 KB

Electroreduction of aromatic dand o-keto esters in the presence of chlorotrimethylsilane and triethylamine gave fiveand six-membered cyclized products. The products were transformed to the corresponding a-hydroxy ketones.