Experimental evidence on the existence of an exo-pi-allyl complex intermediate in the Pd-0-catalyzed alkylation of a bicyclic allylic diacetate with stabilized nucleophiles

Authors
Brunel, JM Maffei, M Muchow, G Buono, G
Citation
Jm. Brunel et al., Experimental evidence on the existence of an exo-pi-allyl complex intermediate in the Pd-0-catalyzed alkylation of a bicyclic allylic diacetate with stabilized nucleophiles, EUR J ORG C, (5), 2001, pp. 1009-1012
Citations number
19
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
5
Year of publication
2001
Pages
1009 - 1012
Database
ISI
SICI code
1434-193X(200103):5<1009:EEOTEO>2.0.ZU;2-U
Abstract
The Pd-0-catalyzed alkylation of 1 by sodiodimethylmalonate led to the form ation of two tricyclic diastereomers 2a and 2b. The structure of the major endo diastereomer 2b has been confirmed by NMR experiments and X-ray struct ure analysis. This stereochemistry is in accordance with the formation of a n exo cationic (pi -allyl)palladium intermediate.