Seven-Membered Rings through Metal-Free Rearrangement Mediated by Hypervalent Iodine

A versatile and metal-free approach for the synthesis of carbocycles and of heterocycles bearing seven- and eight-membered rings is described. The strategy is based on ring expansion of 1-vinylcycloalkanols (or the corresponding silyl or methyl ether) mediated by the hypervalent iodine reagent HTIB...

Descripción completa

Detalles Bibliográficos
Autores principales: Silva, Siguara Bastos Lemos, Torre, Adriana Della, de Carvalho, João Ernesto, Ruiz, Ana Lúcia Tasca Gois, Silva, Luiz F.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2015
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6272645/
https://www.ncbi.nlm.nih.gov/pubmed/25599151
http://dx.doi.org/10.3390/molecules20011475
Descripción
Sumario:A versatile and metal-free approach for the synthesis of carbocycles and of heterocycles bearing seven- and eight-membered rings is described. The strategy is based on ring expansion of 1-vinylcycloalkanols (or the corresponding silyl or methyl ether) mediated by the hypervalent iodine reagent HTIB (PhI(OH)OTs). Reaction conditions can be easily adjusted to give ring expansion products bearing different functional groups. A route to medium-ring lactones was also developed.

Ejemplares similares