Roberts, Edward, Sançon, Julien P. and Sweeney, Joseph B. (2005) A New Class of Ammonium Ylid for [2,3]-Sigmatropic Rearrangement Reactions: ene-endo-Spiro Ylids. Organic Letters, 7 (10). pp. 2075-2078. ISSN 1523-7060

The first examples of sigmatropic rearrangements of ene-endo-spirocyclic, tetrahydropyridine-derived ammonium ylids are reported. Thus, spiro[6.7]-ylids rearrange primarily by a [2,3]-pathway, whereas the analogous [6.6]-ylids rearrange by [1,2]- and [2,3]-mechanisms in roughly equal proportions. This method serves as a rapid entry to the core of a range of alkaloids bearing a pyrrolo[1,2-a]azepine or octahydroindolizidine nucleus.

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