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Evidence of Formation of anexo-π-Allyl Complex Intermediate in the Pd0-Catalyzed Alkylation of a Bicyclic Allylic Diacetate with Stabilized Carbon Nucleophiles
- Source :
- European Journal of Organic Chemistry. 2000:1799-1803
- Publication Year :
- 2000
- Publisher :
- Wiley, 2000.
-
Abstract
- The palladium(0)-catalyzed alkylation of 2,3-bis(acetoxymethyl)bicyclo[2.2.1]hepta-2,5-diene 1 with malonate-type enolates as nucleophiles is investigated. A monoalkylated product is formed first, and undergoes (depending on the nucleophile used) a second intramolecular reaction leading to spirocyclopropane-annulated bicyclo[2.2.1]heptene derivatives 5. The formation of endo spirobicyclic cyclopropanes adducts as major isomer is rationalized by assuming formation of an intermediate exo-(π-allyl)palladium complex.
Details
- ISSN :
- 10990690 and 1434193X
- Volume :
- 2000
- Database :
- OpenAIRE
- Journal :
- European Journal of Organic Chemistry
- Accession number :
- edsair.doi...........56244af815837d33c7306baf196c9d59