𝔖 Bobbio Scriptorium
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Solid phase Diels–Alder/retro Diels–Alder reactions. A new method for traceless linker strategy

✍ Scribed by Luis Blanco; Robert Bloch; Emmanuelle Bugnet; Sandrine Deloisy

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
84 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis

A resin-bound furan has been efficiently synthesized from Merrifield resin. This new polymer reacts with an acetylenic dienophile to afford a thermally stable Diels-Alder adduct. Transformation of the adduct by Michael reaction with thiophenol has allowed an easy retro Diels-Alder reaction. This 'safety-catch' procedure leads to the formation of a chemically and stereochemically pure alkene and to the regeneration of the polymer-bound furan.

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Lewis acid mediated thienium cation diels-alder reaction: A new method for regio- and stereoselective functionalization of 1,3-dienes
✍ Kaoru Fuji; Subhash P. Khanapure; Manabu Node; Takeo Kawabata; Akichika Ito 📂 Article 📅 1985 🏛 Elsevier Science 🌐 French ⚖ 189 KB

Under the influence of aluminum chloride the B-ethylthionitroolefin results in the formation of the thienium cation, which reacts with a variety of 1,3-dienes in the Diels-Alder sense. The cleavage of the resulting ring provides in one pot the 1,4-functionalized olefins in regio-and stereoselective