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The intramolecular silyl modified sakurai (ISMS) reaction. A novel and highly convergent synthesis of oxocenes

✍ Scribed by Abdelaziz Mekhalfia; István E Markó; Harry Adams


Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
248 KB
Volume
32
Category
Article
ISSN
0040-4039

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✦ Synopsis


By employing the intramolecular version of the SMS reaction, oxocenes, including spiroethers and spiroketals, can be prepared in a highly convergent, one-step operation.

In the preceding communicationl, we have described our initial findings on a novel and powerful methodology -The Silyl Modified Sakurai (SMS) reaction -for the preparation of homoallylic ethers directly from carbonyl derivatives. We envisoned that the intramolecular variant of the SMS reaction might provide a simple and efficient route towards the synthesis of spiroethers and spiroketals*.

In this Letter, we report some of our results on the successful


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Regiocontrol in the intramolecular silyl
✍ István E. Markó; Abdelaziz Mekhalfia 📂 Article 📅 1992 🏛 Elsevier Science 🌐 French ⚖ 248 KB

The ISMS reaction, which initially afforded a mixture of regioisomeric olefins, can now be controlled to produce only the exocyclic alkene. The ISMS methodology was used in a highly efficient synthesis of a Dacus oleae pheromone 8.