A new class of ammonium ylid for [2,3]-sigmatropic rearrangement reactions: ene-endo-spiro ylidsRoberts, E., Sancon, J.P. and Sweeney, J.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 Full text not archived in this repository. It is advisable to refer to the publisher's version if you intend to cite from this work. See Guidance on citing. To link to this item DOI: 10.1021/ol050691+ Abstract/SummaryThe 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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