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New Organocatalytic Asymmetric Synthesis of Highly Substituted Chiral 2-Oxospiro-[indole-3,4′-(1′,4′-dihydropyridine)] Derivatives

Herein, we report our preliminary results concerning the first promising asymmetric synthesis of highly functionalized 2-oxospiro-[indole-3,4′-(1′,4′-dihydropyridine)] via the reaction of an enamine with isatylidene malononitrile derivatives in the presence of a chiral base organocatalyst. The moder...

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Detalles Bibliográficos
Autores principales: Auria-Luna, Fernando, Marqués-López, Eugenia, Mohammadi, Somayeh, Heiran, Roghayeh, Herrera, Raquel P.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6331859/
https://www.ncbi.nlm.nih.gov/pubmed/26334263
http://dx.doi.org/10.3390/molecules200915807
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author Auria-Luna, Fernando
Marqués-López, Eugenia
Mohammadi, Somayeh
Heiran, Roghayeh
Herrera, Raquel P.
author_facet Auria-Luna, Fernando
Marqués-López, Eugenia
Mohammadi, Somayeh
Heiran, Roghayeh
Herrera, Raquel P.
author_sort Auria-Luna, Fernando
collection PubMed
description Herein, we report our preliminary results concerning the first promising asymmetric synthesis of highly functionalized 2-oxospiro-[indole-3,4′-(1′,4′-dihydropyridine)] via the reaction of an enamine with isatylidene malononitrile derivatives in the presence of a chiral base organocatalyst. The moderate, but promising, enantioselectivity observed (30%–58% ee (enantiomeric excess)) opens the door to a new area of research for the asymmetric construction of these appealing spirooxindole skeletons, whose enantioselective syntheses are still very limited.
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spelling pubmed-63318592019-01-24 New Organocatalytic Asymmetric Synthesis of Highly Substituted Chiral 2-Oxospiro-[indole-3,4′-(1′,4′-dihydropyridine)] Derivatives Auria-Luna, Fernando Marqués-López, Eugenia Mohammadi, Somayeh Heiran, Roghayeh Herrera, Raquel P. Molecules Communication Herein, we report our preliminary results concerning the first promising asymmetric synthesis of highly functionalized 2-oxospiro-[indole-3,4′-(1′,4′-dihydropyridine)] via the reaction of an enamine with isatylidene malononitrile derivatives in the presence of a chiral base organocatalyst. The moderate, but promising, enantioselectivity observed (30%–58% ee (enantiomeric excess)) opens the door to a new area of research for the asymmetric construction of these appealing spirooxindole skeletons, whose enantioselective syntheses are still very limited. MDPI 2015-08-31 /pmc/articles/PMC6331859/ /pubmed/26334263 http://dx.doi.org/10.3390/molecules200915807 Text en © 2015 by the authors. Licensee MDPI, 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/4.0/).
spellingShingle Communication
Auria-Luna, Fernando
Marqués-López, Eugenia
Mohammadi, Somayeh
Heiran, Roghayeh
Herrera, Raquel P.
New Organocatalytic Asymmetric Synthesis of Highly Substituted Chiral 2-Oxospiro-[indole-3,4′-(1′,4′-dihydropyridine)] Derivatives
title New Organocatalytic Asymmetric Synthesis of Highly Substituted Chiral 2-Oxospiro-[indole-3,4′-(1′,4′-dihydropyridine)] Derivatives
title_full New Organocatalytic Asymmetric Synthesis of Highly Substituted Chiral 2-Oxospiro-[indole-3,4′-(1′,4′-dihydropyridine)] Derivatives
title_fullStr New Organocatalytic Asymmetric Synthesis of Highly Substituted Chiral 2-Oxospiro-[indole-3,4′-(1′,4′-dihydropyridine)] Derivatives
title_full_unstemmed New Organocatalytic Asymmetric Synthesis of Highly Substituted Chiral 2-Oxospiro-[indole-3,4′-(1′,4′-dihydropyridine)] Derivatives
title_short New Organocatalytic Asymmetric Synthesis of Highly Substituted Chiral 2-Oxospiro-[indole-3,4′-(1′,4′-dihydropyridine)] Derivatives
title_sort new organocatalytic asymmetric synthesis of highly substituted chiral 2-oxospiro-[indole-3,4′-(1′,4′-dihydropyridine)] derivatives
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6331859/
https://www.ncbi.nlm.nih.gov/pubmed/26334263
http://dx.doi.org/10.3390/molecules200915807
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