Abstract
The reaction of functionalized nitroalkanes with electrophiles such as Michael acceptors and aldehydes is one of the most exploited procedures for the synthesis of new carbon-carbon bonds. Conversion of the nitro group in the adduct into a carbonyl derivative usually provides a rapid entry to dicarbonyl systems that are amenable to further synthetic transformation into a plethora of important targets.
Highlights
Polyfunctionalized derivatives containing a dicarbonyl moiety are valuable intermediates in organic synthesis since they can be transformed into a plethora of important target compounds such as cyclopentenones, furans, pyrroles, thiophenes and other heterocyclic systems.[1,2,3,4,5,6,7,8] Classical methods for the synthesis of dicarbonyl derivatives usually involve an addition reaction of a metal enolate with a carboxylic acid ester or with a Michael acceptor
Many synthetic approaches directed to the preparation of dicarbonyl derivatives enjoy the utilization of nitroalkanes as useful reagents for building up the alkyl framework
The ability of the nitro group to be converted into a carbonyl group represents the key step of most of the procedures devoted to the preparation of 1,4-dicarbonyl derivatives
Summary
Polyfunctionalized derivatives containing a dicarbonyl moiety are valuable intermediates in organic synthesis since they can be transformed into a plethora of important target compounds such as cyclopentenones, furans, pyrroles, thiophenes and other heterocyclic systems.[1,2,3,4,5,6,7,8] Classical methods for the synthesis of dicarbonyl derivatives usually involve an addition reaction of a metal enolate with a carboxylic acid ester or with a Michael acceptor. The aim of this review is to discuss the utilization of nitroalkanes as nucleophilic reagents for the synthesis of dicarbonyl derivatives using a strategy involving a nucleophilic addition of the nitro derivative followed by a nitro to carbonyl conversion These procedures are usually accomplished by a two-step synthesis, there are several examples in which this overall transformation can be carried out in a ‘one-pot’ system realizing a more efficient process. Conjugate addition of nitroalkanes to enones and enoates provides a rapid entry to the corresponding γ-nitro carbonyl derivatives that can undergo a Nef reaction giving 1,4-dicarbonyl compounds This procedure represents one of the most exploited methods to prepare such difunctionalized derivatives that find a number of applications in the synthesis of important target molecules. The same process can be realized in a ‘one-pot’ reaction, using hydrogen peroxide to carry out the nitro to carbonyl conversion
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