6533b7d3fe1ef96bd1260a87

RESEARCH PRODUCT

A new palladium(II)-catalyzed [3,3] aza-Claisen rearrangement of 3-allyloxy-5-aryl-1,2,4-oxadiazoles

Antonio Palumbo PiccionelloGianfranco Fontana

subject

StereochemistryArylOrganic ChemistryCationic polymerizationchemistry.chemical_elementSettore CHIM/06 - Chimica OrganicaSigmatropic reactionBiochemistryCarroll rearrangementAza-Claisen 124-Oxadiazoles 124-Oxadiazolones PalladiumCatalysisClaisen rearrangementchemistry.chemical_compoundchemistryDrug DiscoveryPalladiumCope rearrangement

description

Abstract A new efficient palladium(II)-catalyzed [3,3] aza-Claisen, formal sigmatropic rearrangement of 3-allyloxy-5-aryl-1,2,4-oxadiazoles was developed. The mechanism was studied by analyzing the regiochemical and stereochemical course of the reaction. The results obtained indicated the intervention of a cationic pallada-cycle similar to the one postulated for the Cope rearrangement of 1,5-dienes.

yearjournalcountryeditionlanguage
2011-02-01
10.1016/j.tetlet.2010.12.058http://hdl.handle.net/10447/54621