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

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Title: Enantioselective Michael Addition of Aldehydes to Maleimides Organocatalyzed by a Chiral Primary Amine-Salicylamide
Authors: Torregrosa-Chinillach, Alejandro | Moragues, Adrien | Pérez-Furundarena, Haritz | Chinchilla, Rafael | Gómez Bengoa, Enrique | Guillena, Gabriela
Research Group/s: Catálisis Estereoselectiva en Síntesis Orgánica (CESO)
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 | Maleimides | Aldehydes
Knowledge Area: Química Orgánica
Issue Date: 12-Dec-2018
Publisher: MDPI
Citation: Torregrosa-Chinillach A, Moragues A, Pérez-Furundarena H, Chinchilla R, Gómez-Bengoa E, Guillena G. Enantioselective Michael Addition of Aldehydes to Maleimides Organocatalyzed by a Chiral Primary Amine-Salicylamide. Molecules. 2018; 23(12):3299. doi:10.3390/molecules23123299
Abstract: 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.
Sponsor: We thank the financial support from the Spanish Ministerio de Economía, Industria y Competitividad (CTQ2015-66624-P and CTQ201788171-P) and the University of Alicante (VIGROB-173). A.M. thanks SIGMA Clermont Chemistry Engineering Graduate School for an ERASMUS+ fellowship. We also thank the Basque Government (GIC15/03, IT1033-16) for financial support, and IZO/SGI SGIker of UPV/EHU for human and technical support.
URI: http://hdl.handle.net/10045/84768
ISSN: 1420-3049
DOI: 10.3390/molecules23123299
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: https://doi.org/10.3390/molecules23123299
Appears in Collections:INV - CESO - Artículos de Revistas

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