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Título: | Trifluorosulfonylation Cascade in Allenols: Stereocontrolled Synthesis of Bis(triflyl)enones |
Autor: | Lázaro-Milla, Carlos; Macicior, Jon CSIC; Yanai, H.; Almendros, Pedro CSIC ORCID | Palabras clave: | Allenes Fluorine Metal-free reactions Selectivity Synthetic methods |
Fecha de publicación: | 2020 | Editor: | John Wiley & Sons | Citación: | Chemistry - A European Journal 26: 8983-8989 (2020) | Resumen: | Herein, we report investigations embodying the first example of reversal of the native regioselectivity in the reaction of allenols with electrophiles. The effortlessness of C−C bond formation, mild reaction conditions, neither catalysts nor light irradiation, and exquisite selectivity, both in terms of functional-group tolerance and chemo-, site-, and stereo-selectivity, converts this trifluorosulfonylation-rearrangement sequence into an appealing protocol for the preparation of novel functionalized enones. The synthetic utility of this method has been validated by the conversion of the initially prepared bis(triflyl)enones into a variety of bis(triflyl)-functionalized molecules such as 1,3-dienes, allylic alcohols, pyrroles, pyrazoles, and chromenes. Besides, DFT calculations have provided a reliable understanding of observed selectivity. | Versión del editor: | http://dx.doi.org/10.1002/chem.202001236 | URI: | http://hdl.handle.net/10261/220983 | DOI: | 10.1002/chem.202001236 | Identificadores: | doi: 10.1002/chem.202001236 issn: 0947-6539 e-issn: 1521-3765 |
Aparece en las colecciones: | (IQOG) Artículos |
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