%0 Journal Article
%T Seven-Membered Rings through Metal-Free Rearrangement Mediated by Hypervalent Iodine
%A Siguara Bastos Lemos Silva
%A Adriana Della Torre
%A Joo Ernesto de Carvalho
%A Ana L¨²cia Tasca Gois Ruiz
%A Luiz F. Silva
%J Molecules
%P 1475-1494
%D 2015
%I MDPI AG
%R 10.3390/molecules20011475
%X 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.
%K hypervalent iodine
%K ring expansion
%K rearrangement
%K seven-membered ring
%K antiproliferative activity
%U http://www.mdpi.com/1420-3049/20/1/1475