Ávila Freire, Ángel, Chinchilla, Rafael, Fiser, Béla, Gómez Bengoa, Enrique, Nájera, Carmen
Enantioselective Michael addition of isobutyraldehyde to nitroalkenes organocatalyzed by chiral primary amine-guanidines
Tetrahedron: Asymmetry. 2014, 25(5): 462-467. doi:10.1016/j.tetasy.2014.02.006
URI: http://hdl.handle.net/10045/37268
DOI: 10.1016/j.tetasy.2014.02.006
ISSN: 0957-4166 (Print)
Abstract: 
Primary amine-guanidines derived from trans-cyclohexane-1,2-diamines are used as organocatalysts for the enantioselective conjugate addition of isobutyraldehyde to arylated and heteroarylated nitroalkenes. The reaction was performed in the presence of imidazole as the additive in aqueous DMF as the solvent at 0 °C. The corresponding Michael adducts bearing a new stereocenter were obtained in high yields and with enantioselectivities of up to 80%. Theoretical calculations are used to justify the observed sense of the stereoinduction.
Keywords:Enantioselective Michael addition, Isobutyraldehyde, Nitroalkenes, Organocatalyzed, Chiral primary amine-guanidines
Elsevier
info:eu-repo/semantics/article