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Molecules
Volume 23
Issue 1
10.3390/molecules23010141
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Open AccessArticle

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

by
José R. Martínez-Guillén
1,
Jesús Flores-Ferrándiz
1,
Cecilia Gómez
1,
Enrique Gómez-Bengoa
2,* and
Rafael Chinchilla
1,*
1
Department of Organic Chemistry, Faculty of Sciences, and Institute of Organic Synthesis (ISO), University of Alicante, P.O. Box 99, 03080 Alicante, Spain
2
Department of Organic Chemistry I, University of the Basque Country, P.O. Box 1072, 20080 San Sebastíán, Spain
*
Authors to whom correspondence should be addressed.
Molecules 2018, 23(1), 141; https://doi.org/10.3390/molecules23010141
Received: 25 December 2017 / Revised: 8 January 2018 / Accepted: 9 January 2018 / Published: 11 January 2018
(This article belongs to the Special Issue Stereogenic Centers)
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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. View Full-Text
Keywords: organocatalysis; asymmetric synthesis; Michael addition; nitroalkenes organocatalysis; asymmetric synthesis; Michael addition; nitroalkenes
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited

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MDPI and ACS Style

Martínez-Guillén, J.R.; 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, 141.

AMA Style

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.

Chicago/Turabian Style

Martínez-Guillén, José R.; Flores-Ferrándiz, Jesús; Gómez, Cecilia; Gómez-Bengoa, Enrique; Chinchilla, Rafael. 2018. "Asymmetric Conjugate Addition of α,α-Disubstituted Aldehydes to Nitroalkenes Organocatalyzed by Chiral Monosalicylamides from trans-Cyclohexane-1,2-Diamines" Molecules 23, no. 1: 141.

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