Acyclic α-nitro ketones : a versatile class of α-functionalized ketones in organic synthesis

Abstract

α-Nitro ketones are an emerging class of molecules in organic synthesis, due to the presence on two adjacent positions of the carbonyl group and the carbon–nitro group moiety, that offers a new reactivity pattern, peculiar to a-nitro ketones. However, α-nitro cycloalkanones and acyclic α-nitro ketones have unlike reactivities and are utilized differently. The ring cleavage, promoted by external or internal nucleophiles (zip reactions), represents the main behaviour of cyclic α-nitro ketones, and these retro-Claisen condensations have already been exhaustively reviewed, while this report is mainly devoted to provide a comprehensive coverage of the synthesis, reactivity and possible transformations of acyclic α-nitro ketones, as well as their utilization in several interesting synthetic applications. Some common reactivities of both cyclic and acyclic α-nitro ketones will be also reported.