Asymmetric Conjugate Addition of α,α-Disubstituted Aldehydes to Nitroalkenes Organocatalyzed by Chiral Monosalicylamides from trans-Cyclohexane-1,2-Diamines

Primary amine-salicylamides derived from chiral trans-cyclohexane-1,2-diamines are used as organocatalysts for the enantioselective conjugate addition of α,α-disubstituted aldehydes to arylated and heteroarylated nitroalkenes. The reaction is performed in the presence of 4-dimethylaminopyridine as a...

Descripción completa

Detalles Bibliográficos
Autores principales: Martínez-Guillén, José R., Flores-Ferrándiz, Jesús, Gómez, Cecilia, Gómez-Bengoa, Enrique, Chinchilla, Rafael
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6017890/
https://www.ncbi.nlm.nih.gov/pubmed/29324713
http://dx.doi.org/10.3390/molecules23010141
_version_ 1783334849558347776
author Martínez-Guillén, José R.
Flores-Ferrándiz, Jesús
Gómez, Cecilia
Gómez-Bengoa, Enrique
Chinchilla, Rafael
author_facet Martínez-Guillén, José R.
Flores-Ferrándiz, Jesús
Gómez, Cecilia
Gómez-Bengoa, Enrique
Chinchilla, Rafael
author_sort Martínez-Guillén, José R.
collection PubMed
description Primary amine-salicylamides derived from chiral trans-cyclohexane-1,2-diamines are used as organocatalysts for the enantioselective conjugate addition of α,α-disubstituted aldehydes to arylated and heteroarylated nitroalkenes. The reaction is performed in the presence of 4-dimethylaminopyridine as an additive in dichloromethane as a solvent at room temperature. The corresponding enantioenriched γ-nitroaldehydes are obtained with enantioselectivities up to 95%. Theoretical calculations are used to justify the reasons of the stereoinduction.
format Online
Article
Text
id pubmed-6017890
institution National Center for Biotechnology Information
language English
publishDate 2018
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-60178902018-11-13 Asymmetric Conjugate Addition of α,α-Disubstituted Aldehydes to Nitroalkenes Organocatalyzed by Chiral Monosalicylamides from trans-Cyclohexane-1,2-Diamines Martínez-Guillén, José R. Flores-Ferrándiz, Jesús Gómez, Cecilia Gómez-Bengoa, Enrique Chinchilla, Rafael Molecules Article Primary amine-salicylamides derived from chiral trans-cyclohexane-1,2-diamines are used as organocatalysts for the enantioselective conjugate addition of α,α-disubstituted aldehydes to arylated and heteroarylated nitroalkenes. The reaction is performed in the presence of 4-dimethylaminopyridine as an additive in dichloromethane as a solvent at room temperature. The corresponding enantioenriched γ-nitroaldehydes are obtained with enantioselectivities up to 95%. Theoretical calculations are used to justify the reasons of the stereoinduction. MDPI 2018-01-11 /pmc/articles/PMC6017890/ /pubmed/29324713 http://dx.doi.org/10.3390/molecules23010141 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
Martínez-Guillén, José R.
Flores-Ferrándiz, Jesús
Gómez, Cecilia
Gómez-Bengoa, Enrique
Chinchilla, Rafael
Asymmetric Conjugate Addition of α,α-Disubstituted Aldehydes to Nitroalkenes Organocatalyzed by Chiral Monosalicylamides from trans-Cyclohexane-1,2-Diamines
title Asymmetric Conjugate Addition of α,α-Disubstituted Aldehydes to Nitroalkenes Organocatalyzed by Chiral Monosalicylamides from trans-Cyclohexane-1,2-Diamines
title_full Asymmetric Conjugate Addition of α,α-Disubstituted Aldehydes to Nitroalkenes Organocatalyzed by Chiral Monosalicylamides from trans-Cyclohexane-1,2-Diamines
title_fullStr Asymmetric Conjugate Addition of α,α-Disubstituted Aldehydes to Nitroalkenes Organocatalyzed by Chiral Monosalicylamides from trans-Cyclohexane-1,2-Diamines
title_full_unstemmed Asymmetric Conjugate Addition of α,α-Disubstituted Aldehydes to Nitroalkenes Organocatalyzed by Chiral Monosalicylamides from trans-Cyclohexane-1,2-Diamines
title_short Asymmetric Conjugate Addition of α,α-Disubstituted Aldehydes to Nitroalkenes Organocatalyzed by Chiral Monosalicylamides from trans-Cyclohexane-1,2-Diamines
title_sort asymmetric conjugate addition of α,α-disubstituted aldehydes to nitroalkenes organocatalyzed by chiral monosalicylamides from trans-cyclohexane-1,2-diamines
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6017890/
https://www.ncbi.nlm.nih.gov/pubmed/29324713
http://dx.doi.org/10.3390/molecules23010141
work_keys_str_mv AT martinezguillenjoser asymmetricconjugateadditionofaadisubstitutedaldehydestonitroalkenesorganocatalyzedbychiralmonosalicylamidesfromtranscyclohexane12diamines
AT floresferrandizjesus asymmetricconjugateadditionofaadisubstitutedaldehydestonitroalkenesorganocatalyzedbychiralmonosalicylamidesfromtranscyclohexane12diamines
AT gomezcecilia asymmetricconjugateadditionofaadisubstitutedaldehydestonitroalkenesorganocatalyzedbychiralmonosalicylamidesfromtranscyclohexane12diamines
AT gomezbengoaenrique asymmetricconjugateadditionofaadisubstitutedaldehydestonitroalkenesorganocatalyzedbychiralmonosalicylamidesfromtranscyclohexane12diamines
AT chinchillarafael asymmetricconjugateadditionofaadisubstitutedaldehydestonitroalkenesorganocatalyzedbychiralmonosalicylamidesfromtranscyclohexane12diamines

Ejemplares similares