[4 + 2]-Cycloaddition Reactions between β-Acceptor-Substituted Enamines and 2-Vinylindole Radical Cations Acting as Hetero-Dienes
- 1 January 1996
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 61 (12) , 4136-4143
- https://doi.org/10.1021/jo951551o
Abstract
[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.Keywords
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