Use of polymer-supported amines in catalytic nitroaldol reaction of nitroalkanes with aldehydes

Abstract

An efficient catalytic synthesis of 2-nitroalcohols has been achieved through a catalytic nitroaldol (Henry) reaction promoted by polymer-supported amines. These achiral and chiral polymer-bound amines show general utility in their reactions with a variety of aromatic and functionalized aldehyde acceptors. Moreover, the catalyst can be reused without loss of activity.

Pore size control and organocatalytic properties of nanostructured silica hybrid materials containing amino and ammonium groups

“…59,60 Here, we studied in particular the Henry reaction of benzaldehyde with nitroethane (Scheme 4, R ¼ CH 3 ). 61,62 The results of these experiments are summarized in Table 4.…”

Asymmetric Bioreductions of β-Nitro Acrylates as a Route to Chiral β2-Amino Acids

“…The required β-nitroacrylates 3a − g were prepared by a two-step sequence (Scheme ). Henry reactions were carried out using a solid-phase base along with the appropriate α-keto ester (either commercially available or prepared by the method of Macritchie et al) and nitroalkane 13a. Spectral data for nitroaldol adducts 2a − e , g matched those reported previously. , These were converted to the corresponding nitroacrylates via mesylate derivatives .…”

“…Henry reactions were carried out using a solid-phase base along with the appropriate α-keto ester (either commercially available or prepared by the method of Macritchie et al) and nitroalkane 13a. Spectral data for nitroaldol adducts 2a − e , g matched those reported previously. , These were converted to the corresponding nitroacrylates via mesylate derivatives . Both 2-alkyl-substituted nitroacrylates 3a and b were obtained predominantly in the ( E )-form, whereas the ( Z )-isomers predominated for 3-substituted alkenes 3c − g .…”