Asymmetric Friedel-Crafts Alkylation of Indole with Chalcones Catalyzed by Chiral Phosphoric Acids

The reaction of indole with chalcones, to give Michael-type adducts, was found to occur with good efficiency (up to 98% yield) and moderate enantioselectivity (up to 52% e.e.) in the presence of a chiral BINOL-based phosphoric acid. Furthermore, the alkylation products can be obtained in much higher...

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Autores principales: Scettri, Arrigo, Villano, Rosaria, Acocella, Maria Rosaria
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Molecular Diversity Preservation International 2009
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6255435/
https://www.ncbi.nlm.nih.gov/pubmed/19701143
http://dx.doi.org/10.3390/molecules14083030
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author Scettri, Arrigo
Villano, Rosaria
Acocella, Maria Rosaria
author_facet Scettri, Arrigo
Villano, Rosaria
Acocella, Maria Rosaria
author_sort Scettri, Arrigo
collection PubMed
description The reaction of indole with chalcones, to give Michael-type adducts, was found to occur with good efficiency (up to 98% yield) and moderate enantioselectivity (up to 52% e.e.) in the presence of a chiral BINOL-based phosphoric acid. Furthermore, the alkylation products can be obtained in much higher e.e.s after one only crystallization.
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spelling pubmed-62554352018-11-30 Asymmetric Friedel-Crafts Alkylation of Indole with Chalcones Catalyzed by Chiral Phosphoric Acids Scettri, Arrigo Villano, Rosaria Acocella, Maria Rosaria Molecules Article The reaction of indole with chalcones, to give Michael-type adducts, was found to occur with good efficiency (up to 98% yield) and moderate enantioselectivity (up to 52% e.e.) in the presence of a chiral BINOL-based phosphoric acid. Furthermore, the alkylation products can be obtained in much higher e.e.s after one only crystallization. Molecular Diversity Preservation International 2009-08-13 /pmc/articles/PMC6255435/ /pubmed/19701143 http://dx.doi.org/10.3390/molecules14083030 Text en © 2009 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland. This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Scettri, Arrigo
Villano, Rosaria
Acocella, Maria Rosaria
Asymmetric Friedel-Crafts Alkylation of Indole with Chalcones Catalyzed by Chiral Phosphoric Acids
title Asymmetric Friedel-Crafts Alkylation of Indole with Chalcones Catalyzed by Chiral Phosphoric Acids
title_full Asymmetric Friedel-Crafts Alkylation of Indole with Chalcones Catalyzed by Chiral Phosphoric Acids
title_fullStr Asymmetric Friedel-Crafts Alkylation of Indole with Chalcones Catalyzed by Chiral Phosphoric Acids
title_full_unstemmed Asymmetric Friedel-Crafts Alkylation of Indole with Chalcones Catalyzed by Chiral Phosphoric Acids
title_short Asymmetric Friedel-Crafts Alkylation of Indole with Chalcones Catalyzed by Chiral Phosphoric Acids
title_sort asymmetric friedel-crafts alkylation of indole with chalcones catalyzed by chiral phosphoric acids
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6255435/
https://www.ncbi.nlm.nih.gov/pubmed/19701143
http://dx.doi.org/10.3390/molecules14083030
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AT acocellamariarosaria asymmetricfriedelcraftsalkylationofindolewithchalconescatalyzedbychiralphosphoricacids

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