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Synthesis of vinylcyclopropanes via palladium-catalyzed coupling of cyclopropylzinc halides with vinyl iodides. Total syntheses of (±) -prezizanol and (±)-prezizaene

✍ Scribed by Edward Piers; Michel Jean; Peter S. Marrs

Book ID
104227299
Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
265 KB
Volume
28
Category
Article
ISSN
0040-4039

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✦ Synopsis

Palladium(O)-catalyzed coupling of cyclopropylzinc halides, readily prepared from the corresponding cyclopropyl(tri-D-butyl)stannanes, with vinyl iodides provides good yields of functionalized vinylcyclopropanes.

The coupling reaction is used as a key step in total syntheses of the sesquiterpenoids (f)-prezizanol and (+)-prezizaene.

📜 SIMILAR VOLUMES

Palladium/copper (I) halide catalyzed st
Palladium/copper (I) halide catalyzed stereospecific couplings of 1,2-difluorovinylstannanes with aryl iodides and vinyl halides
✍ Long Lu; Donald J Burton 📂 Article 📅 1997 🏛 Elsevier Science 🌐 French ⚖ 206 KB

Palladium/copper (I) halide catalyzed cross couplings of (E)-and (Z)-I,2difluorovinyistannanes with aryl iodides and vinyl halides proceeded at room temperature to stereospecifically give 1,2-disubstituted-l,2-difluoroolef'ms and 1,2difluoro or 1,2,3,4-tetrafluorosubstituted dienes in good to excell