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Gold(i)-catalyzed cycloisomerization of vinylidenecyclopropane-enes via carbene or non-carbene processes

Gold catalyzed cycloisomerization of aromatic ring tethered vinylidenecyclopropane-enes provides a divergent synthetic protocol for the construction of O-containing fused heterocycles through controllable carbene or non-carbene related processes. The carbene induced process features a new amphiphili...

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Detalles Bibliográficos
Autores principales: Li, De-Yao, Wei, Yin, Marek, Ilan, Tang, Xiang-Ying, Shi, Min
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5949847/
https://www.ncbi.nlm.nih.gov/pubmed/29861890
http://dx.doi.org/10.1039/c5sc01806d
Descripción
Sumario:Gold catalyzed cycloisomerization of aromatic ring tethered vinylidenecyclopropane-enes provides a divergent synthetic protocol for the construction of O-containing fused heterocycles through controllable carbene or non-carbene related processes. The carbene induced process features a new amphiphilic strategy to generate a gold carbene via a rearrangement of vinylidenecyclopropane. Whereas, the electronic effect of the ortho-substituents switches the reaction mode onto the non-carbene related process, from which five- or six-membered rings are selectively produced through allyl-migration.