TY - JOUR
T1 - Enantioselective addition of aryl ketones and acetone to nitroalkenes organocatalyzed by carbamate-monoprotected cyclohexa-1,2-diamines
AU - Flores-Ferrándiz, Jesús
AU - Stiven, Alexander
AU - Sotorríos, Lia
AU - Gómez-Bengoa, Enrique
AU - Chinchilla, Rafael
PY - 2015/9/15
Y1 - 2015/9/15
N2 - Enantiomerically pure carbamate-monoprotected trans-cyclohexane-1,2-diamines are used as chiral organocatalysts for the addition of aryl ketones and acetone to nitroalkenes to give enantioenriched β-substituted γ-nitroketones. The reaction was performed in the presence of 3,4-dimethoxybenzoic acid as an additive, in chloroform as the solvent at room temperature, achieving enantioselectivities up to 96%. Theoretical calculations are used to justify the observed sense of the stereoinduction.
AB - Enantiomerically pure carbamate-monoprotected trans-cyclohexane-1,2-diamines are used as chiral organocatalysts for the addition of aryl ketones and acetone to nitroalkenes to give enantioenriched β-substituted γ-nitroketones. The reaction was performed in the presence of 3,4-dimethoxybenzoic acid as an additive, in chloroform as the solvent at room temperature, achieving enantioselectivities up to 96%. Theoretical calculations are used to justify the observed sense of the stereoinduction.
U2 - 10.1016/j.tetasy.2015.07.011
DO - 10.1016/j.tetasy.2015.07.011
M3 - Article
VL - 26
SP - 970
EP - 979
JO - Tetrahedron: Asymmetry
JF - Tetrahedron: Asymmetry
IS - 17
ER -