Hetero‐Cope‐Umlagerungen. 4. Mitteilung. Regiokontrollierte Indolsynthesen

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Abstract
Hetero‐Cope‐Rearrangements, Regio‐Controlled Synthesis of IndolesThe reaction of O‐deprotonated N‐phenylhydroxylamines 1 with various electron‐deficient allenes 2, 14, 16 gives, via Michael addition and Cope‐rearrangement, substituted anilines 5, which are easily convertible into indoles 6. In this manner, sulfoxides 17, serve as equivalents of 2‐vinylindoles. Diels‐Alder reaction with this 2‐vinylindole equivalent followed by indolisation affords isoquinuclidine derivative 21 which may be a useful precursor for the preparation of Iboga alkaloids.