Tetrahedron Letters

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

G Fontana, AP Piccionello

Index: Fontana, Gianfranco; Palumbo Piccionello, Antonio Tetrahedron Letters, 2011 , vol. 52, # 8 p. 884 - 886

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Citation Number: 4

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.