American Chemical Society
jo7b02355_si_001.pdf (4.55 MB)

The Palladium-Catalyzed Intramolecular Alder-Ene Reactions of O- and N‑Linked 1,6-Enynes Incorporating Triethylsilyl Capping Groups

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journal contribution
posted on 2017-10-24, 00:00 authored by Jeremy Nugent, Eliška Matoušová, Martin G. Banwell, Anthony C. Willis
A series of O- and N-linked 1,6-enynes (e.g., 11) have been prepared with each subjected to a palladium-catalyzed intramolecular Alder-ene (IMAE) reaction, thus producing the isomeric and cyclic 1,4-diene (e.g., 12). These processes proceed most effectively when a triethylsilyl group is attached to the alkyne moiety and so generating alkenylsilanes that can be manipulated in various useful ways, including via iododesilylation (to give, for example, iodoalkene 62).