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Título: | Direct Access to 2,3,4,6-Tetrasubstituted Tetrahydro-2H-pyrans via Tandem SN2′–Prins Cyclization |
Autor: | Scoccia, Jimena; Pérez, Sixto J.; Sinka, Victoria CSIC ORCID; Cruz, Daniel A. CSIC ORCID; López-Soria, Juan M. CSIC; Fernández, Israel; Martín, Víctor S. CSIC ORCID; Miranda, Pedro O. CSIC ORCID ; Padrón, Juan I. CSIC ORCID | Fecha de publicación: | 31-ago-2017 | Editor: | American Chemical Society | Citación: | Organic Letters 19(18): 4834-4837 (2017) | Resumen: | A new, direct, and diastereoselective synthesis of activated 2,3,4,6-tetrasubstituted tetrahydro-2H-pyrans is described. In this reaction, iron(III) catalyzed an SN2′–Prins cyclization tandem process leading to the creation of three new stereocenters in one single step. These activated tetrahydro-2H-pyran units are easily derivatizable through CuAAC conjugations in order to generate multifunctionalized complex molecules. DFT calculations support the in situ SN2′ reaction as a preliminary step in the Prins cyclization. | Versión del editor: | https://doi.org/10.1021/acs.orglett.7b02270 | URI: | http://hdl.handle.net/10261/184912 | DOI: | 10.1021/acs.orglett.7b02270 | ISSN: | 1523-7060 | E-ISSN: | 1523-7052 |
Aparece en las colecciones: | (IPNA) Artículos |
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