Publication: Nuevos métodos catalíticos de ciclación/transposición de alenos basados en metales de transición
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2018-08-29
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Universidad Complutense de Madrid
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Abstract
En los últimos 20 años, los alenos y cumulenos se han convertido en grupos funcionales versátiles con una reactividad única, permitiendo acceder a una gran variedad de compuestos de alto interés químico y biológico. En especial, las reacciones de ciclación de alenos con un sustituyente nucleófilo catalizadas por metales de transición han experimentado un notable desarrollo en los últimos años. Por otro lado, los compuestos heterocíclicos que contienen un núcleo - lactámico y/o indólico en su estructura son particularmente relevantes debido a su presencia en productos naturales y sintéticos con actividad biológica, tales como antibióticos, aminoácidos u hormonas. Finalmente, los compuestos fluorados presentan una importante actividad biológica gracias a su alta lipofilia y estabilidad metabólica. Asimismo, la desaromatización de indoles ha ganado especial importancia en Síntesis Orgánica debido a la alta bioactividad que presentan las indolinas resultantes. Por este motivo, en los últimos años se han descrito un gran número de métodos de fluoración de indoles funcionalizados, que permiten obtener de manera directa una gran variedad de indolinas fluoradas...
During the last 20 years the chemistry of allenes has been extensively studied due to their interesting reactivity. Allenes and cumulenes have metamorphosed from a laboratory curiosity to a versatile and uniquely reactive functional groups, allowing chemists to prepare a variety of compounds of chemical and biological interest. Among the abroad range of reactions of this kind of compounds, intramolecular cyclization of allenes and cumulenes bearing a nucleophilic substituent are of particular interest. The appearance of regioselectivity problems in these cyclization processes has led to the development of a wide spectrum of metal- catalyzed methodologies that aim to control this issue. On the other hand, among heterocycles, β-lactam and indole derivatives attracted greater attention due to their biological and pharmacological activities such as antibacterial, enzyme inhibitors, neurotransmitters and antitumorals. Finally, fluoroorganic molecules feature peculiar biological activities because of their improved lipophilicity and metabolic stability. Besides, the dearomatization of indoles has received considerable attention in organic synthesis because of the bioactivity of the resulting indolines. In the last years, considerable efforts have been devoted to the fluorination of functionalised indoles because this methodology is a direct entry to diverse fluorinated indoline structures...
During the last 20 years the chemistry of allenes has been extensively studied due to their interesting reactivity. Allenes and cumulenes have metamorphosed from a laboratory curiosity to a versatile and uniquely reactive functional groups, allowing chemists to prepare a variety of compounds of chemical and biological interest. Among the abroad range of reactions of this kind of compounds, intramolecular cyclization of allenes and cumulenes bearing a nucleophilic substituent are of particular interest. The appearance of regioselectivity problems in these cyclization processes has led to the development of a wide spectrum of metal- catalyzed methodologies that aim to control this issue. On the other hand, among heterocycles, β-lactam and indole derivatives attracted greater attention due to their biological and pharmacological activities such as antibacterial, enzyme inhibitors, neurotransmitters and antitumorals. Finally, fluoroorganic molecules feature peculiar biological activities because of their improved lipophilicity and metabolic stability. Besides, the dearomatization of indoles has received considerable attention in organic synthesis because of the bioactivity of the resulting indolines. In the last years, considerable efforts have been devoted to the fluorination of functionalised indoles because this methodology is a direct entry to diverse fluorinated indoline structures...
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Tesis inédita de la Universidad Complutense de Madrid, Facultad de Ciencias Químicas, Departamento de Química Orgánica I, leída el 19-01-2017