Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/199615
Type: Artigo de periódico
Title: Substrate-directable Heck Reactions With Arenediazonium Salts. The Regio- And Stereoselective Arylation Of Allylamine Derivatives And Applications In The Synthesis Of Naftifine And Abamines.
Author: Prediger, Patrícia
Barbosa, Laís Ferreira
Génisson, Yves
Correia, Carlos Roque Duarte
Abstract: The palladium-catalyzed, substrate-directable Heck-Matsuda reaction of allylamine derivatives with arenediazonium salts is reported. The reaction proceeds under mild conditions, with excellent regio- and stereochemical control as a function of coordinating groups present in the allylamine substrate. The distance between the olefin moiety and the carbonylic system seems to play a key role regarding the regiocontrol. The method presents itself as robust, as simple to carry out, and with wide synthetic scope concerning the allylic substrates and the type of arenediazonium employed. The synthetic potential of the method is illustrated by the short total syntheses of the bioactive compounds naftifine, abamine, and abamine SG.
Rights: fechado
Identifier DOI: 10.1021/jo201105z
Address: http://www.ncbi.nlm.nih.gov/pubmed/21877731
Date Issue: 2011
Appears in Collections:Artigos e Materiais de Revistas Científicas - Unicamp

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