Nitroalkanes as Key Compounds for the Synthesis of Amino Derivatives

Abstract

The carbanion stabilizing effect of the nitro group makes nitroalkanes ideal reagents in carbon-carbon bond formation. Once introduced in a molecular framework, the nitro group is amenable to further transformations including reduction to primary amines. The aim of this review is to explore the utilization of nitroalkanes as effective substrates for the preparation of important target compounds featured by the amino group. These will include simple primary amines, diamines, amino acids, piperidines, pyrrolidines and heteroaromatic derivatives. A particular emphasis will be placed on the synthesis of enantioenriched amino derivatives mediated by organocatalysts or organometallic complexes. Keywords: Amines, asymmetric synthesis, nitroalkanes, nucleophilic additions, reductions, peroxytrifluoroacetic acid, urea-hydrogen peroxide complex, trifluoroacetic anhydride, anti cancer drug threo-dihydrosphingosine, adrenoceptor, norphenylephrine, antihypertensive drug, ritodrine, retroaldol process, enantioselective aza-Henry reaction