Drawing from a Pool of Radicals for the Design of Selective Enyne Cyclizations

Despite the possibility of intermolecular attack at four different locations, the Bu3Sn-mediated radical cyclization of aromatic enynes is surprisingly selective. The observed reaction path originates from the least stable of the equilibrating pool of isomeric radicals produced by intermolecular Bu3...

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Bibliographic Details
Published in:Organic letters 2013-11, Vol.15 (22), p.5650-5653
Main Authors: Mondal, Sayantan, Mohamed, Rana K, Manoharan, Mariappan, Phan, Hoa, Alabugin, Igor V
Format: Article
Language:English
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Summary:Despite the possibility of intermolecular attack at four different locations, the Bu3Sn-mediated radical cyclization of aromatic enynes is surprisingly selective. The observed reaction path originates from the least stable of the equilibrating pool of isomeric radicals produced by intermolecular Bu3Sn attack at the π-bonds of substrates. The radical pool components are kinetically self-sorted via 5-exo-trig closure, the fastest of the four possible cyclizations. The resulting Sn-substituted indenes are capable of further transformations in reactions with electrophiles.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol4028072