Abstract
The formation of bicyclic amines by the intramolecular cyclization of 4-aza-6-methoxycarbonyl-5-hexenyl radicals is described. The direct attachment of a nitrogen atom to the double bond changes the electronic nature of the alkene such that the cyclization is less efficient than the all carbon analogue or the other aza-substituted 5-hexenyl cyclizations.The reaction has been used in a short, convenient synthesis of a variety of indolizidines from methyl nicotinate. In addition, the cyclization was used as the key step in a short synthesis of (±)-epilupinine from methyl nicotinate.
Published Version
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