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Título: | Iron(III)-Catalyzed Prins Cyclization towards the Synthesis of trans-fused Bicyclic Tetrahydropyrans |
Autor: | Pérez, Sixto J.; Miranda, Pedro O. CSIC ORCID ; Cruz, Daniel A. CSIC ORCID; Fernández, Israel; Martín, Víctor S. CSIC ORCID; Padrón, Juan I. CSIC ORCID | Palabras clave: | Sustainable Metal Catalysis Bicyclic Tetrahydropyrans Prins Cyclization Cyclic ethers Iron |
Fecha de publicación: | 2015 | Editor: | Thieme | Citación: | Synthesis 47(12): 1791-1798 (2015) | Resumen: | trans-Fused bicyclic tetrahydropyrans have been synthesized through an intramolecular Prins cyclization catalyzed by iron(III). The cyclization process is stereoselective, leading exclusively to an all-cis configuration in the newly generated ring. This useful methodology allows for easy access to a variety of bicyclic ethers present in a wide range of bioactive natural products. Remarkably, the cyclization reaction works well when more challenging aldehydes bearing a functional group, such as a double bond or an acetate, are used. In addition, we present a computational study which rationalizes the results and explains the complete cis stereoselectivity in the newly formed tetrahydropyran ring. | Versión del editor: | https://doi.org/10.1055/s-0034-1380013 | URI: | http://hdl.handle.net/10261/181133 | DOI: | 10.1055/s-0034-1380013 | ISSN: | 0039-7881 | E-ISSN: | 1437-210X |
Aparece en las colecciones: | (IPNA) Artículos |
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accesoRestringido.pdf | 15,38 kB | Adobe PDF | Visualizar/Abrir |
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