Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/75213
Type: Artigo de periódico
Title: Stereoselective heck-matsuda arylations of chiral dihydrofurans with arenediazonium tetrafluoroborates; An efficient enantioselective total synthesis of (-)-isoaltholactone
Author: Meira, PRR
Moro, AV
Correia, CRD
Abstract: The Heck-Matsuda arylation of chiral 2-(S)-hydroxymethyl dihydrofurans (endocyclic enolethers) and its derivatives, employing arenediazonium tetrafluoroborates, was developed into a highly efficient, practical and diastereoselective synthetic process. This methodology was applied to the total synthesis of the styryllactone (-)-isoaltholactone in seven steps with an overall yield of similar to 25%, from the readily available chiral 2-hydroxymethyldihydrofuran. The strategy permits the synthesis of several other aromatic analogues of isoaltholactone.
Subject: Heck reaction
palladium
diazonium compounds
catalysis
stereoselectivity
Country: Alemanha
Editor: Georg Thieme Verlag Kg
Rights: aberto
Identifier DOI: 10.1055/s-2007-983781
Date Issue: 2007
Appears in Collections:Artigos e Materiais de Revistas Científicas - Unicamp

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