jo951551o_si_001.pdf (850.32 kB)
[4 + 2]-Cycloaddition Reactions between β-Acceptor-Substituted Enamines and 2-Vinylindole Radical Cations Acting as Hetero-Dienes
journal contribution
posted on 1996-06-14, 00:00 authored by Christoph F. Gürtler, Eberhard Steckhan, Siegfried Blechert[4 + 2]-Cycloaddition reactions between 2-vinylindoles
acting as hetero-dienes and β-acceptor
substituted cyclic and acyclic enamines can be induced by formation of
2-vinylindole radical cations
either via anodic oxidation or photoelectron transfer (PET) using
catalytic amounts of triarylpyrylium tetrafluoroborates as sensitizers. In this way,
pyrido[1,2-a]indoles or
indolo[1,2-a]hexahydro-1,8-naphthyridines are formed in one step with complete regio- and
stereochemical control.