A New Class of Ammonium Ylid for [2,3]-Sigmatropic Rearrangement Reactions: e ne-endo-Spiro Ylids
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. Th...
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| Veröffentlicht in: | Organic letters 2005-05, Vol.7 (10), p.2075-2078 |
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| container_title | Organic letters |
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| creator | Roberts, Edward Sançon, Julien P Sweeney, J. B |
| description | 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. |
| doi_str_mv | 10.1021/ol050691+ |
| format | Article |
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B</creatorcontrib><title>A New Class of Ammonium Ylid for [2,3]-Sigmatropic Rearrangement Reactions: e ne-endo-Spiro Ylids</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>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. 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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.</abstract><pub>American Chemical Society</pub><doi>10.1021/ol050691+</doi><tpages>4</tpages></addata></record> |
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| ispartof | Organic letters, 2005-05, Vol.7 (10), p.2075-2078 |
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| language | eng |
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| source | ACS Publications |
| title | A New Class of Ammonium Ylid for [2,3]-Sigmatropic Rearrangement Reactions: e ne-endo-Spiro Ylids |
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