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Iodine(III)-Promoted Ring Expansion of 1-Vinylcycloalkanol Derivatives:  A Metal-Free Approach toward Seven-Membered Rings

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posted on 06.03.2008, 00:00 by Luiz F. Silva,, Ramon S. Vasconcelos, Mário A. Nogueira
A versatile and metal-free approach for the synthesis of molecules bearing seven- and eight-membered rings is described. The strategy is based on the ring expansion of 1-vinylcycloalkanols (or the corresponding silyl or methyl ether) mediated by the hypervalent iodine reagent HTIB (PhI(OH)OTs). The reaction condition can be easily adjusted to give seven-membered rings bearing different functional groups. A route to medium-ring lactones was also developed.