Seven-Membered Rings through Metal-Free Rearrangement Mediated by Hypervalent Iodine
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...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2015-01-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/20/1/1475 |
| _version_ | 1828386106861682688 |
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| author | Siguara Bastos Lemos Silva Adriana Della Torre João Ernesto de Carvalho Ana Lúcia Tasca Gois Ruiz Luiz F. Silva |
| author_facet | Siguara Bastos Lemos Silva Adriana Della Torre João Ernesto de Carvalho Ana Lúcia Tasca Gois Ruiz Luiz F. Silva |
| author_sort | Siguara Bastos Lemos Silva |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-10T05:31:32Z |
| format | Article |
| id | doaj.art-220143a459de4ceba472f0e99494fdc5 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-10T05:31:32Z |
| publishDate | 2015-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-220143a459de4ceba472f0e99494fdc52022-12-22T02:00:31ZengMDPI AGMolecules1420-30492015-01-012011475149410.3390/molecules20011475molecules20011475Seven-Membered Rings through Metal-Free Rearrangement Mediated by Hypervalent IodineSiguara Bastos Lemos Silva0Adriana Della Torre1João Ernesto de Carvalho2Ana Lúcia Tasca Gois Ruiz3Luiz F. Silva4Departamento de Química Fundamental, Instituto de Química, Universidade de São Paulo, Av. Prof. Lineu Prestes, 748, CP 26077, São Paulo-SP CEP 05513-970, BrazilDivision of Pharmacology and Toxicology, Multidisciplinary Center for Chemical, Biological and Agricultural, State University of Campinas, 6171, Campinas-SP CEP 13081-970, BrazilDivision of Pharmacology and Toxicology, Multidisciplinary Center for Chemical, Biological and Agricultural, State University of Campinas, 6171, Campinas-SP CEP 13081-970, BrazilDivision of Pharmacology and Toxicology, Multidisciplinary Center for Chemical, Biological and Agricultural, State University of Campinas, 6171, Campinas-SP CEP 13081-970, BrazilDepartamento de Química Fundamental, Instituto de Química, Universidade de São Paulo, Av. Prof. Lineu Prestes, 748, CP 26077, São Paulo-SP CEP 05513-970, BrazilA 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.http://www.mdpi.com/1420-3049/20/1/1475hypervalent iodinering expansionrearrangementseven-membered ringantiproliferative activity |
| spellingShingle | Siguara Bastos Lemos Silva Adriana Della Torre João Ernesto de Carvalho Ana Lúcia Tasca Gois Ruiz Luiz F. Silva Seven-Membered Rings through Metal-Free Rearrangement Mediated by Hypervalent Iodine Molecules hypervalent iodine ring expansion rearrangement seven-membered ring antiproliferative activity |
| title | Seven-Membered Rings through Metal-Free Rearrangement Mediated by Hypervalent Iodine |
| title_full | Seven-Membered Rings through Metal-Free Rearrangement Mediated by Hypervalent Iodine |
| title_fullStr | Seven-Membered Rings through Metal-Free Rearrangement Mediated by Hypervalent Iodine |
| title_full_unstemmed | Seven-Membered Rings through Metal-Free Rearrangement Mediated by Hypervalent Iodine |
| title_short | Seven-Membered Rings through Metal-Free Rearrangement Mediated by Hypervalent Iodine |
| title_sort | seven membered rings through metal free rearrangement mediated by hypervalent iodine |
| topic | hypervalent iodine ring expansion rearrangement seven-membered ring antiproliferative activity |
| url | http://www.mdpi.com/1420-3049/20/1/1475 |
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