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Addition of Z-Vinylic Higher Order Cyanocuprates to Enones Followed by O-Functionalization

✍ Scribed by D.N. Moraes; R.E. Barrientos-Astigarraga; P. Castelani; J.V. Comasseto

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
190 KB
Volume
56
Category
Article
ISSN
0040-4020

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✦ Synopsis

AbstractÐTransmetalation reaction between Z-vinylic tellurides and higher order cyanocuprates generated the corresponding Z-vinylic cyanocuprates. Conjugate addition of these cuprates to enones followed by O-functionalization led to silyl enol ethers, vinyl phosphates and vinyl tri¯ates. The vinyl tri¯ates were transformed into highly unsaturated systems by coupling with alkynes or with Z-vinyl zinc chlorides under Pd (0) catalysis.

📜 SIMILAR VOLUMES

Addition of Z-vinylic higher order cyano
Addition of Z-vinylic higher order cyanocuprates to hindered enones. The influence of the reaction conditions
✍ M.A. Araújo; R.E. Barrientos-Astigarraga; R.M. Ellensohn; J.V. Comasseto 📂 Article 📅 1999 🏛 Elsevier Science 🌐 French ⚖ 175 KB

Z-Vinylic higher order cyanocuprates, prepared from the corresponding Z-vinylic tellurides, react efficiently with hindered enones in THF/BF3-Et20 or in diethyl ether. In neat THF the hindered enones fail to react with Z-vinyl cyanocuprates prepared in this way.