Tetrahedron p. 5269 - 5282 (1989)
Update date:2022-08-04
Topics:
Beckwith, Athelstan L. J.
Westwood, Steven W.
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.
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