Formal [3+2] Cycloaddition of Nitrosoallenes with Carbonyl and Nitrile Compounds to Form Functional Cyclic Nitrones

The synthesis of functional cyclic nitrones via [3+2] cycloadditions of allenamide-derived nitrosoallenes with carbonyl/nitrile compounds, including ketones, esters, and nitriles, is presented herein. Rapid carbon–carbon, carbon–oxygen, and carbon–nitrogen bond formations were achieved with <i>in situ</i> prepared nitrosoallenes, and densely substituted oxacyclic and carbocyclic nitrones containing tetrasubstituted carbon centers were successfully synthesized. The spirocyclic nitrone products synthesized from cyclic dicarbonyl compounds underwent the unique skeletal rearrangements to cyclic α-ketonitrones

Synthesis of α‑Substituted Enoximes with Nucleophiles via Nitrosoallenes

This paper reports nitrosoallene-mediated synthesis of α-substituted enoximes. Nucleophilic substitution of nitrosoallenes, a novel chemical species prepared from allenyl <i>N</i>-hydroxysulfonamides, afforded α-functionalized enoximes. Introduction of various nucleophiles proceeded smoothly to form C–N, C–O, C–S, C–F, and C–C bonds in the presence of azodicarboxylates

Synthesis of α‑Substituted Enoximes with Nucleophiles via Nitrosoallenes

This paper reports nitrosoallene-mediated synthesis of α-substituted enoximes. Nucleophilic substitution of nitrosoallenes, a novel chemical species prepared from allenyl <i>N</i>-hydroxysulfonamides, afforded α-functionalized enoximes. Introduction of various nucleophiles proceeded smoothly to form C–N, C–O, C–S, C–F, and C–C bonds in the presence of azodicarboxylates