Generation and Reactivity of Aza-Oxyallyl Cationic Intermediates: Aza-[4+ 3] Cycloaddition Reactions for Heterocycle Synthesis

CS Jeffrey, KL Barnes, JA Eickhoff…

Index: Jeffrey, Christopher S.; Barnes, Korry L.; Eickhoff, John A.; Carson, Christopher R. Journal of the American Chemical Society, 2011 , vol. 133, # 20 p. 7688 - 7691

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Citation Number: 35

Abstract

Aza-[4+ 3] cycloadditions of putative aza-oxyallyl cationic intermediates and cyclic dienes are reported. The intermediate is generated by the dehydrohalogenation of α-haloamides. The reaction is general to a variety of α-haloamides and is diastereoselective. Computational and experimental data suggest that an N-alkoxy substituent stabilizes the aza-oxyallyl cationic intermediate.