Abstract
AbstractThe nature and influence of the N‐sulfonyl group in aza‐Prins cyclization and the reactivity of the six‐membered aza‐cycle generated has been studied. The aza‐Prins cyclization of γ,δ‐unsaturated amines with a tosyl group at the nitrogen atom produces 2‐alkyl‐4‐halo‐1‐tosyl‐1,2,5,6‐tetrahydropyridines with a halovinyl function, extraordinarily stable to further derivatization and detosylation conditions. To modulate the reactivity of such aza‐cycles, a general study of the aza‐Prins cyclization reaction was performed with several sulfonamides. Ring formation occurs satisfactorily with both N‐nosyl and N‐mesylamines providing optimal conditions for further synthetic transformations. To exemplify the scope of this methodology, a short synthesis of the alkaloid coniine was successfully carried out.
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