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Article

Seven-Membered Rings through Metal-Free Rearrangement Mediated by Hypervalent Iodine

1
Departamento de Química Fundamental, Instituto de Química, Universidade de São Paulo, Av. Prof. Lineu Prestes, 748, CP 26077, São Paulo-SP CEP 05513-970, Brazil
2
Division of Pharmacology and Toxicology, Multidisciplinary Center for Chemical, Biological and Agricultural, State University of Campinas, 6171, Campinas-SP CEP 13081-970, Brazil
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Molecules 2015, 20(1), 1475-1494; https://doi.org/10.3390/molecules20011475
Received: 2 December 2014 / Accepted: 8 January 2015 / Published: 15 January 2015
(This article belongs to the Section Organic Chemistry)
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. View Full-Text
Keywords: hypervalent iodine; ring expansion; rearrangement; seven-membered ring; antiproliferative activity hypervalent iodine; ring expansion; rearrangement; seven-membered ring; antiproliferative activity
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MDPI and ACS Style

Silva, S.B.L.; Torre, A.D.; De Carvalho, J.E.; Ruiz, A.L.T.G.; Silva, L.F., Jr. Seven-Membered Rings through Metal-Free Rearrangement Mediated by Hypervalent Iodine. Molecules 2015, 20, 1475-1494. https://doi.org/10.3390/molecules20011475

AMA Style

Silva SBL, Torre AD, De Carvalho JE, Ruiz ALTG, Silva LF Jr.. Seven-Membered Rings through Metal-Free Rearrangement Mediated by Hypervalent Iodine. Molecules. 2015; 20(1):1475-1494. https://doi.org/10.3390/molecules20011475

Chicago/Turabian Style

Silva, Siguara B.L., Adriana D. Torre, João E. De Carvalho, Ana L.T.G. Ruiz, and Luiz F. Silva Jr. 2015. "Seven-Membered Rings through Metal-Free Rearrangement Mediated by Hypervalent Iodine" Molecules 20, no. 1: 1475-1494. https://doi.org/10.3390/molecules20011475

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