通过高价碘介导的无金属重排反应构建七元环。

Seven-membered rings through metal-free rearrangement mediated by hypervalent iodine.

作者信息

Silva Siguara Bastos Lemos, Torre Adriana Della, de Carvalho João Ernesto, Ruiz Ana Lúcia Tasca Gois, Silva Luiz F

机构信息

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.

Division of Pharmacology and Toxicology, Multidisciplinary Center for Chemical, Biological and Agricultural, State University of Campinas, 6171, Campinas-SP CEP 13081-970, Brazil.

出版信息

Molecules. 2015 Jan 15;20(1):1475-94. doi: 10.3390/molecules20011475.

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.