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

Authors:Nieto, Sonia
Sayago, Francisco J.
Laborda, Pedro
Soler, Tatiana
Cativiela, Carlos
Urriolabeitia, Esteban P.
Issue Date:2011
Citation:Tetrahedron 67(23): 4185-4191 (2011)
Abstract: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.
Identifiers:doi: 10.1016/j.tet.2011.04.064
issn: 0040-4020
Appears in Collections:(ICMA) Artículos

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