A new and practical PIFA-promoted olefin amidohydroxylation: six- versus five-membered ring formation

• DOI: 10.1016/s0040-4039(03)00670-1
• Publication Date: 2003-04-07T19:40:02Z
• Authors: Sonia Serna; Imanol Tellitu; Esther Domı́nguez; Isabel Moreno; Raúl SanMartı́n
• Keywords: 01 natural sciences; 0104 chemical sciences

A novel access to the isoindolinone and isoquinolin-2-one skeletons from adequately substituted aromatic precursors is described. The key intramolecular cyclization step was performed by the action of phenyliodine(III)bis(trifluoroacetate) (PIFA) on the corresponding vinyl or allyl substituted N-(p-methoxyphenyl)benzamide derivatives leading to the heterocyclic compounds through 5-exo-trig and 6-exo-trig processes, respectively.