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

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Title: Asymmetric Conjugate Addition of α,α-Disubstituted Aldehydes to Nitroalkenes Organocatalyzed by Chiral Monosalicylamides from trans-Cyclohexane-1,2-Diamines
Authors: Martínez Guillén, José Ramón | Flores Ferrándiz, Jesús | Gómez Lucas, Cecilia | Gómez Bengoa, Enrique | Chinchilla, Rafael
Research Group/s: Catálisis Estereoselectiva en Síntesis Orgánica (CESO) | Nuevos Materiales y Catalizadores (MATCAT)
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica
Keywords: Organocatalysis | Asymmetric synthesis | Michael addition | Nitroalkenes
Knowledge Area: Química Orgánica
Issue Date: 11-Jan-2018
Publisher: MDPI
Citation: Martínez-Guillén JR, Flores-Ferrándiz J, Gómez C, Gómez-Bengoa E, Chinchilla R. Asymmetric Conjugate Addition of α,α-Disubstituted Aldehydes to Nitroalkenes Organocatalyzed by Chiral Monosalicylamides from trans-Cyclohexane-1,2-Diamines. Molecules. 2018; 23(1):141. doi:10.3390/molecules23010141
Abstract: 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.
Sponsor: We thank the financial support from the Spanish Ministerio de Economía, Industria y Competitividad (CTQ2015-66624-P) and the University of Alicante (VIGROB-173, UAUSTI17-06). J.F.-F. thanks the Vicerrectorado de Investigación y Transferencia del Conocimiento de la Universidad de Alicante for a fellowship. We also thank the Basque Government (GIC15/03, IT1033-16) for financial support, and the General Research Services (IZO/SGI SGIker) of the University of the Basque Country for human and technical support.
URI: http://hdl.handle.net/10045/72447
ISSN: 1420-3049
DOI: 10.3390/molecules23010141
Language: eng
Type: info:eu-repo/semantics/article
Rights: © 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/).
Peer Review: si
Publisher version: http://dx.doi.org/10.3390/molecules23010141
Appears in Collections:INV - MATCAT - Artículos de Revistas
INV - CESO - Artículos de Revistas
INV - AMIC - Artículos de Revistas

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