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Asymmetric Conjugate Addition of Ketones to Maleimides Organocatalyzed by a Chiral Primary Amine-Salicylamide

Enantioenriched substituted succinimides are interesting compounds, and their asymmetric organocatalytic synthesis by the conjugated addition of ketones to maleimides has been scarcely explored. This study shows the enantioselective conjugate addition of ketones to maleimides organocatalyzed by a si...

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Autores principales: Torregrosa-Chinillach, Alejandro, Chinchilla, Rafael
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9573004/
https://www.ncbi.nlm.nih.gov/pubmed/36235205
http://dx.doi.org/10.3390/molecules27196668
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author Torregrosa-Chinillach, Alejandro
Chinchilla, Rafael
author_facet Torregrosa-Chinillach, Alejandro
Chinchilla, Rafael
author_sort Torregrosa-Chinillach, Alejandro
collection PubMed
description Enantioenriched substituted succinimides are interesting compounds, and their asymmetric organocatalytic synthesis by the conjugated addition of ketones to maleimides has been scarcely explored. This study shows the enantioselective conjugate addition of ketones to maleimides organocatalyzed by a simple primary amine-salicylamide derived from a chiral trans-cyclohexane-1,2-diamine, which provides the desired succinimides in good to excellent yields (up to 98%) and with moderate to excellent enantioselectivities (up to 99%).
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spelling pubmed-95730042022-10-17 Asymmetric Conjugate Addition of Ketones to Maleimides Organocatalyzed by a Chiral Primary Amine-Salicylamide Torregrosa-Chinillach, Alejandro Chinchilla, Rafael Molecules Article Enantioenriched substituted succinimides are interesting compounds, and their asymmetric organocatalytic synthesis by the conjugated addition of ketones to maleimides has been scarcely explored. This study shows the enantioselective conjugate addition of ketones to maleimides organocatalyzed by a simple primary amine-salicylamide derived from a chiral trans-cyclohexane-1,2-diamine, which provides the desired succinimides in good to excellent yields (up to 98%) and with moderate to excellent enantioselectivities (up to 99%). MDPI 2022-10-07 /pmc/articles/PMC9573004/ /pubmed/36235205 http://dx.doi.org/10.3390/molecules27196668 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Torregrosa-Chinillach, Alejandro
Chinchilla, Rafael
Asymmetric Conjugate Addition of Ketones to Maleimides Organocatalyzed by a Chiral Primary Amine-Salicylamide
title Asymmetric Conjugate Addition of Ketones to Maleimides Organocatalyzed by a Chiral Primary Amine-Salicylamide
title_full Asymmetric Conjugate Addition of Ketones to Maleimides Organocatalyzed by a Chiral Primary Amine-Salicylamide
title_fullStr Asymmetric Conjugate Addition of Ketones to Maleimides Organocatalyzed by a Chiral Primary Amine-Salicylamide
title_full_unstemmed Asymmetric Conjugate Addition of Ketones to Maleimides Organocatalyzed by a Chiral Primary Amine-Salicylamide
title_short Asymmetric Conjugate Addition of Ketones to Maleimides Organocatalyzed by a Chiral Primary Amine-Salicylamide
title_sort asymmetric conjugate addition of ketones to maleimides organocatalyzed by a chiral primary amine-salicylamide
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9573004/
https://www.ncbi.nlm.nih.gov/pubmed/36235205
http://dx.doi.org/10.3390/molecules27196668
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