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Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
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Aldehydes and ketones are prepared from alcohols, alkenes, and alkynes via different reaction pathways. Alcohols are the most commonly used substrates for synthesizing aldehydes and ketones. The conversion of alcohol to aldehyde, which involves the oxidation process, depends on the class of the alcohol used and the strength of the oxidizing agent. For instance, primary alcohol will form an aldehyde when treated with a weak oxidizing agent; however, it gets over-oxidized to a carboxylic acid in...
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By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
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Benzaldehyde, like formaldehyde, lacks an α hydrogen and cannot enolize to form an enolate. Hence, the reaction of benzaldehyde with a ketone in the presence of an aqueous base forms a single crossed product. This reaction is referred to as Claisen–Schmidt condensation.
As the self-condensation of ketones is generally not favored in basic conditions, the self-condensed products do not form in the reaction between ketones and benzaldehyde. The general reaction of Claisen–Schmidt...
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Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an...
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Síntesis enantioselectiva de cetonas α-oxigenadas mediante la inserción de enlaces O-H formales organocatalíticos de

Chenxiao Qian1,2, Ziwei Zhong1, Qingzheng Xu1

  • 1Department of Chemistry and the Hong Kong Branch of Chinese National Engineering Research Centre for Tissue Restoration & Reconstruction, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR 999077, China.

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Este estudio introduce un método organocatalítico sin metales para la síntesis de cetonas enriquecidas con enantio. El nuevo enfoque utiliza ylidos de sulfuro de α-carbonilo para la inserción de enlaces O-H, creando valiosos estereocentros terciarios α-oxigenados.

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Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • Síntesis estereoselectiva

Sus antecedentes:

  • La química de diazocarbonilo a base de metal se utiliza ampliamente para los ésteres, pero tiene menos éxito para las cetonas.
  • El desarrollo de métodos eficientes para la síntesis de cetonas con estereoquímica específica es un desafío.

Objetivo del estudio:

  • Desarrollar un método organocatalítico sin metales para la inserción de enlaces O-H enantioselectivos de ylidos de sulfuro de α-carbonilo.
  • Proporcionar acceso a cetonas altamente enantioenriquecidas con un estereocentro terciario α-oxigenado.

Principales métodos:

  • Organocatálisis con un catalizador quiral de tiourea y ftalimidas de N-hidroxilo.
  • Inserción de enlaces O-H formales enantioselectivos de ylidos de sulfuro de α-carbonilo.
  • Estudios mecánicos, incluidos los cálculos del DFT.

Principales resultados:

  • Síntesis eficiente de cetonas enriquecidas con enantio con un estereocentro terciario α-oxigenado.
  • Demostración de un enfoque sin metales que sea complementario de los métodos existentes.
  • Identificación de la activación del enlace de hidrógeno de los ylidos de sulfonio como el mecanismo de iniciación probable.

Conclusiones:

  • El método organocatalítico desarrollado ofrece una vía novedosa y eficiente para obtener cetonas quirales valiosas.
  • Esta estrategia libre de metales amplía el alcance de la química de yeldos de sulfuro de α-carbonilo.
  • La comprensión del mecanismo catalítico proporciona una base para un mayor diseño y optimización del catalizador.