Enantioselective Michael Addition of Aldehydes to Maleimides Organocatalyzed by a Chiral Primary Amine-Salicylamide

A primary amine-salicylamide derived from chiral trans-cyclohexane-1,2-diamine was used as an organocatalyst for the enantioselective conjugate addition of aldehydes, mainly α,α-disubstituted to N-substituted maleimides. The reaction was performed in toluene as a solvent at room temperature. The cor...

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Autores principales: Torregrosa-Chinillach, Alejandro, Moragues, Adrien, Pérez-Furundarena, Haritz, Chinchilla, Rafael, Gómez-Bengoa, Enrique, Guillena, Gabriela
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6320823/
https://www.ncbi.nlm.nih.gov/pubmed/30545145
http://dx.doi.org/10.3390/molecules23123299
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author Torregrosa-Chinillach, Alejandro
Moragues, Adrien
Pérez-Furundarena, Haritz
Chinchilla, Rafael
Gómez-Bengoa, Enrique
Guillena, Gabriela
author_facet Torregrosa-Chinillach, Alejandro
Moragues, Adrien
Pérez-Furundarena, Haritz
Chinchilla, Rafael
Gómez-Bengoa, Enrique
Guillena, Gabriela
author_sort Torregrosa-Chinillach, Alejandro
collection PubMed
description A primary amine-salicylamide derived from chiral trans-cyclohexane-1,2-diamine was used as an organocatalyst for the enantioselective conjugate addition of aldehydes, mainly α,α-disubstituted to N-substituted maleimides. The reaction was performed in toluene as a solvent at room temperature. The corresponding enantioenriched adducts were obtained with high yields and enantioselectivities up to 94%. Theoretical calculations were used to justify the stereoinduction.
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spelling pubmed-63208232019-01-14 Enantioselective Michael Addition of Aldehydes to Maleimides Organocatalyzed by a Chiral Primary Amine-Salicylamide Torregrosa-Chinillach, Alejandro Moragues, Adrien Pérez-Furundarena, Haritz Chinchilla, Rafael Gómez-Bengoa, Enrique Guillena, Gabriela Molecules Article A primary amine-salicylamide derived from chiral trans-cyclohexane-1,2-diamine was used as an organocatalyst for the enantioselective conjugate addition of aldehydes, mainly α,α-disubstituted to N-substituted maleimides. The reaction was performed in toluene as a solvent at room temperature. The corresponding enantioenriched adducts were obtained with high yields and enantioselectivities up to 94%. Theoretical calculations were used to justify the stereoinduction. MDPI 2018-12-12 /pmc/articles/PMC6320823/ /pubmed/30545145 http://dx.doi.org/10.3390/molecules23123299 Text en © 2018 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 (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Torregrosa-Chinillach, Alejandro
Moragues, Adrien
Pérez-Furundarena, Haritz
Chinchilla, Rafael
Gómez-Bengoa, Enrique
Guillena, Gabriela
Enantioselective Michael Addition of Aldehydes to Maleimides Organocatalyzed by a Chiral Primary Amine-Salicylamide
title Enantioselective Michael Addition of Aldehydes to Maleimides Organocatalyzed by a Chiral Primary Amine-Salicylamide
title_full Enantioselective Michael Addition of Aldehydes to Maleimides Organocatalyzed by a Chiral Primary Amine-Salicylamide
title_fullStr Enantioselective Michael Addition of Aldehydes to Maleimides Organocatalyzed by a Chiral Primary Amine-Salicylamide
title_full_unstemmed Enantioselective Michael Addition of Aldehydes to Maleimides Organocatalyzed by a Chiral Primary Amine-Salicylamide
title_short Enantioselective Michael Addition of Aldehydes to Maleimides Organocatalyzed by a Chiral Primary Amine-Salicylamide
title_sort enantioselective michael addition of aldehydes to maleimides organocatalyzed by a chiral primary amine-salicylamide
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6320823/
https://www.ncbi.nlm.nih.gov/pubmed/30545145
http://dx.doi.org/10.3390/molecules23123299
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