Amongst the various conversions that are known to transform the furan moiety into other functional groups or heterocyclic rings, the Achmatowicz reaction and the corresponding aza‐modification stand out as broadly applicable oxidative rearrangements. Both reactions are synthetically useful transformations resulting either in pyranone or piperidinone structures, containing ample synthetic opportunities for further functionalization. In this review, we will provide a literature overview of the aza‐Achmatowicz reaction, including application of the resulting piperidinones in the synthesis of biologically active compounds and natural products.

A concise stereoselective route providing access to both enantiomers of the bioactive quinolizidine alkaloid lasubine II has been developed. The enantioselectivity was introduced by taking advantage of a proline-catalyzed asymmetric Mannich reaction. Next, the bicyclic system was constructed via a diastereoselective Mannich cyclization and subsequent ring-closing metathesis as the key steps.

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Enantiomerically pure 2,6-disubstituted piperidinones were synthesized from furfural involving an organocatalyzed Mannich reaction, aza-Achmatowicz reaction, and an N-acyliminium ion-mediated coupling step. This approach was also successfully applied to a total synthesis of (-)-sedacryptine and one of its epimers.

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