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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 J.C.
Correia C.R.D.
Abstract: An efficient and stereoselective protocol for the preparation of β,β-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 4aryltetralones allowing the concise formal total syntheses of the therapeutically important psychoactive compounds (± )-indatraline and (± )-sertraline. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
Rights: fechado
Identifier DOI: 10.1002/adsc.200900032
Date Issue: 2009
Appears in Collections:Unicamp - Artigos e Outros Documentos

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