Efficient access to (1H)-isoindolin-1-one-3-carboxylic acid derivatives by orthopalladation and carbonylation of methyl arylglycinate substrates

The orthopalladation of methyl arylglycinate derivatives has been studied. The reaction proceeds efficiently for different electron-withdrawing and electron-releasing substituents at the aryl ring. The carbonylation of the orthopalladated complexes affords, in a single step, substituted (1H)-isoindolin-1-one-3-carboxylates. These compounds constitute valuable synthetic intermediates and can be transformed diastereoselectively into octahydroisoindole-1-carboxylic acid derivatives, an important scaffold in the synthesis of many biologically active compounds. © 2011 Elsevier Ltd. All rights reserved.Financial support from the Spanish Ministerio de Ciencia e Innovación (projects CTQ2008-01784 and CTQ2010-17436) and Gobierno de Aragón (project PI071/09; research groups E21 and E40) is gratefully acknowledged. S. N. thanks to the CSIC (Spain) for a JAE-DOC contract. P. L. thanks to the Spanish Ministerio de Ciencia e Innovación for a predoctoral fellowship.Peer Reviewe