Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/200280
Type: Artigo de periódico
Title: Coumarins From Free Ortho-hydroxy Cinnamates By Heck-matsuda Arylations: A Scalable Total Synthesis Of (r)-tolterodine.
Author: Barancelli, Daniela A
Salles, Airton G
Taylor, Jason G
Correia, Carlos Roque D
Abstract: Free ortho-hydroxy cinnamate ester derivatives are evaluated in the synthesis of structurally diverse 4-aryl-coumarins via a tandem Heck-Matsuda cyclization reaction. Free phenolic groups were considered incompatible with such a reaction, which usually provide the corresponding diazo dyes. A concise and scalable route employing a ligand-free, Pd-catalyzed Heck-Matsuda arylation under aerobic conditions for the preparation of (R)-Tolterodine in high overall yield and ee is also presented.
Subject: Benzhydryl Compounds
Catalysis
Cinnamates
Coumarins
Cresols
Cyclization
Esters
Molecular Structure
Palladium
Phenylpropanolamine
Stereoisomerism
Rights: fechado
Identifier DOI: 10.1021/ol302923f
Address: http://www.ncbi.nlm.nih.gov/pubmed/23190249
Date Issue: 2012
Appears in Collections:Artigos e Materiais de Revistas Científicas - Unicamp

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