Asymmetric Conjugate Addition of α,α-Disubstituted Aldehydes to Nitroalkenes Organocatalyzed by Chiral Monosalicylamides from trans-Cyclohexane-1,2-Diamines
José R. Martínez-Guillén 1, Jesús Flores-Ferrándiz 1, Cecilia Gómez 1, Enrique Gómez-Bengoa 2,*
and Rafael Chinchilla 1,*
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)
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-TextKeywords:
organocatalysis; asymmetric synthesis; Michael addition; nitroalkenes
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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.
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