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  • Title: Iodine(III)-promoted ring expansion of 1-vinylcycloalkanol derivatives: a metal-free approach toward seven-membered rings.
    Author: Silva LF, Vasconcelos RS, Nogueira MA.
    Journal: Org Lett; 2008 Mar 06; 10(5):1017-20. PubMed ID: 18269290.
    Abstract:
    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.
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