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Molecules 2018, 23(1), 141; https://doi.org/10.3390/molecules23010141

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

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.
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. (CC BY 4.0).

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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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