Jongwoo Son
UIC
Electrocyclizations of N-Vinylnitrones and Sigmatropic Rearrangements of N,O-Divinylhydroxylamines: Novel Access to Highly-Substituted Morpholines and Furans
Our research group has developed new transformations involving N-vinylnitrone and N,O-divinylhydroxylamine intermediates to facilitate the synthesis of functionalized molecules and to access novel heterocyclic structures. Recently, we have expanded the scope of these methods to include the synthesis of oxazine-N-oxides through the 6π-electrocyclization of transient N-vinylnitrones and the preparation of N-furanylamides through the addition of N,O-divinylhydroxylamines to electron-deficient allenes. The optimization, scope, and limitations of these new transformations will be discussed to emphasize new fundamental reactivity patterns and a detailed description of the synthetic versatility of these heterocyclic products will be presented to illustrate their utility in facilitating the preparation of sophisticated structures.
Our research group has developed new transformations involving N-vinylnitrone and N,O-divinylhydroxylamine intermediates to facilitate the synthesis of functionalized molecules and to access novel heterocyclic structures. Recently, we have expanded the scope of these methods to include the synthesis of oxazine-N-oxides through the 6π-electrocyclization of transient N-vinylnitrones and the preparation of N-furanylamides through the addition of N,O-divinylhydroxylamines to electron-deficient allenes. The optimization, scope, and limitations of these new transformations will be discussed to emphasize new fundamental reactivity patterns and a detailed description of the synthetic versatility of these heterocyclic products will be presented to illustrate their utility in facilitating the preparation of sophisticated structures.