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...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Molecules (Basel, Switzerland) Switzerland), 2015-01, Vol.20 (1), p.1475-1494
Hauptverfasser:	Silva, Siguara Bastos Lemos, Torre, Adriana Della, de Carvalho, João Ernesto, Ruiz, Ana Lúcia Tasca Gois, Silva, Luiz F
Format:	Artikel
Sprache:	eng
Schlagworte:	antiproliferative activity Cell Line, Tumor Cell Proliferation - drug effects Heterocyclic Compounds - chemistry Heterocyclic Compounds - pharmacology Humans hypervalent iodine Investigations Iodine Iodine - chemistry Metals - chemistry Models, Molecular Organosilicon Compounds - chemistry Palladium Reagents rearrangement ring expansion seven-membered ring
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

Beschreibung
Zusammenfassung:	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.
ISSN:	1420-3049 1420-3049
DOI:	10.3390/molecules20011475