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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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2015
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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. |
format | Online Article Text |
id | pubmed-6331859 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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