Journal of the American Chemical Society, Vol.133, No.20, 7688-7691, 2011
Generation and Reactivity of Aza-Oxyallyl Cationic Intermediates: Aza-[4+3] Cycloaddition Reactions for Heterocycle Synthesis
Aza-[4 + 3] cycloadditions of putative azaoxyallyl cationic intermediates and cyclic dienes are reported. The intermediate is generated by the dehydrohalogenation of alpha-haloamides. The reaction is general to a variety of alpha-haloamides and is diastereoselective. Computational and experimental data suggest that an N-alkoxy substituent stabilizes the aza-oxyallyl cationic intermediate.