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Type: Artigo de periódico
Title: Remarkable Electronic Effect on the Diastereoselectivity of the Heck Reaction of Methyl Cinnamate with Arenediazonium Salts: Formal Total Synthesis of (+/-)-Indatraline and (+/-)-Sertraline
Author: Pastre, JC
Correia, CRD
Abstract: An efficient and stereoselective protocol for the preparation of beta,beta-disubstituted acrylates in good to high yields by means of a Heck-Matsuda arylation was accomplished. The method employs a base- and ligand-free Heck arylation reaction of methyl cinnamate using both electron-deficient and electron-rich arenediazonium salts as electrophiles. The Heck reaction displays a remarkable electronic dependence regarding the diastereoselectivity of the arylation process, which correlates with the electronic nature of the arenediazonium salts employed. A rationale for the observed diastereoselectivity is presented. The overall methodology provides a convenient route to 3-arylindanones and 4-aryltetralones allowing the concise formal total syntheses of the therapeutically important psychoactive compounds (+/-)-indatraline and (+/-)-sertraline.
Subject: arenediazonium salts
Heck reaction
methyl cinnamate
Country: Alemanha
Editor: Wiley-v C H Verlag Gmbh
Citation: Advanced Synthesis & Catalysis. Wiley-v C H Verlag Gmbh, v. 351, n. 9, n. 1217, n. 1223, 2009.
Rights: fechado
Identifier DOI: 10.1002/adsc.200900032
Date Issue: 2009
Appears in Collections:Unicamp - Artigos e Outros Documentos

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