Martínez Guillén, José Ramón, Flores Ferrándiz, Jesús, Gómez, Cecilia, Gómez Bengoa, Enrique, Chinchilla, Rafael
Asymmetric Conjugate Addition of α,α-Disubstituted Aldehydes to Nitroalkenes Organocatalyzed by Chiral Monosalicylamides from trans-Cyclohexane-1,2-Diamines
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
URI: http://hdl.handle.net/10045/72447
DOI: 10.3390/molecules23010141
ISSN: 1420-3049
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.
Keywords:Organocatalysis, Asymmetric synthesis, Michael addition, Nitroalkenes
MDPI
info:eu-repo/semantics/article