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
_version_ 1783377204882702336
author Silva, Siguara Bastos Lemos
Torre, Adriana Della
de Carvalho, João Ernesto
Ruiz, Ana Lúcia Tasca Gois
Silva, Luiz F.
author_facet Silva, Siguara Bastos Lemos
Torre, Adriana Della
de Carvalho, João Ernesto
Ruiz, Ana Lúcia Tasca Gois
Silva, Luiz F.
author_sort Silva, Siguara Bastos Lemos
collection PubMed
description 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.
format Online
Article
Text
id pubmed-6272645
institution National Center for Biotechnology Information
language English
publishDate 2015
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-62726452018-12-28 Seven-Membered Rings through Metal-Free Rearrangement Mediated by Hypervalent Iodine Silva, Siguara Bastos Lemos Torre, Adriana Della de Carvalho, João Ernesto Ruiz, Ana Lúcia Tasca Gois Silva, Luiz F. Molecules Article 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. MDPI 2015-01-15 /pmc/articles/PMC6272645/ /pubmed/25599151 http://dx.doi.org/10.3390/molecules20011475 Text en © 2015 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Silva, Siguara Bastos Lemos
Torre, Adriana Della
de Carvalho, João Ernesto
Ruiz, Ana Lúcia Tasca Gois
Silva, Luiz F.
Seven-Membered Rings through Metal-Free Rearrangement Mediated by Hypervalent Iodine
title Seven-Membered Rings through Metal-Free Rearrangement Mediated by Hypervalent Iodine
title_full Seven-Membered Rings through Metal-Free Rearrangement Mediated by Hypervalent Iodine
title_fullStr Seven-Membered Rings through Metal-Free Rearrangement Mediated by Hypervalent Iodine
title_full_unstemmed Seven-Membered Rings through Metal-Free Rearrangement Mediated by Hypervalent Iodine
title_short Seven-Membered Rings through Metal-Free Rearrangement Mediated by Hypervalent Iodine
title_sort seven-membered rings through metal-free rearrangement mediated by hypervalent iodine
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6272645/
https://www.ncbi.nlm.nih.gov/pubmed/25599151
http://dx.doi.org/10.3390/molecules20011475
work_keys_str_mv AT silvasiguarabastoslemos sevenmemberedringsthroughmetalfreerearrangementmediatedbyhypervalentiodine
AT torreadrianadella sevenmemberedringsthroughmetalfreerearrangementmediatedbyhypervalentiodine
AT decarvalhojoaoernesto sevenmemberedringsthroughmetalfreerearrangementmediatedbyhypervalentiodine
AT ruizanaluciatascagois sevenmemberedringsthroughmetalfreerearrangementmediatedbyhypervalentiodine
AT silvaluizf sevenmemberedringsthroughmetalfreerearrangementmediatedbyhypervalentiodine

Ejemplares similares