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Iodine(III)-promoted ring expansion of 1-vinylcycloalkanol derivatives: A metal-free approach toward seven-membered rings

Instituto de Química, Universidade de São Paulo, Avenida Professor Lineu Prestes, 748, CP 26077, CEP 05513-970 São Paulo SP, Brazil.
Organic Letters (Impact Factor: 6.32). 04/2008; 10(5):1017-20. DOI: 10.1021/ol800048f
Source: PubMed

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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