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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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Generation and trapping of alkene radical cations under nonoxidizing conditions: formation of six-membered rings by exo- and endo-mode cyclizations.

[reaction: see text] It is demonstrated that alkene radical cations generated by the radical ionic fragmentation of beta-(phosphatoxy)alkyl radicals undergo efficient nucleophilic capture by amines in either the 6-exo or 6-endo modes, leading to six-membered nitrogen heterocycles. Suitable placement of an alkene enables the juxtaposition of a radical cyclization resulting in the formation of both the indolizidine and 1-azabicyclo[3.2.1]octane skeleta.[1]

References

  1. Generation and trapping of alkene radical cations under nonoxidizing conditions: formation of six-membered rings by exo- and endo-mode cyclizations. Crich, D., Neelamkavil, S. Org. Lett. (2002) [Pubmed]
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