The reactivity of nitrones in cycloadditions and related reactions is revisited by introducing a topological perspective. In particular, the study of electron localization function (ELF) along a reaction pathway allows evaluating bond reorganization showing that in several cases the bonds are formed in a sequential way, the second one being formed once the first one is already formed. Both classical 1,3-dipolar cycloadditions and Mannich-type reactions revealed unexpected features often underestimated in classical mechanistic studies.

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The reaction of aromatic nitroso derivatives with enolizable carbonyl compounds (nitroso aldol reaction) to give either α-hydroxyamino or α-aminoxycarbonyls is an important synthetic method. This review illustrates the recent advances in rendering the process regio-and enantioselective as well as catalytic. By employing metal and organic catalysts one can generate a range of α-amino (α-oxyamination) and α-hydroxy (α-aminoxylation) carbonyl derivatives with total regioselectivity and high levels of enantiomeric excess.

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