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Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
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Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
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One of the methods for preparing symmetrical or unsymmetrical acid anhydrides involves the treatment of acid chlorides with the sodium salt of carboxylic acids. The reaction proceeds via a nucleophilic acyl substitution.
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Síntesis enantioselectiva de anilidos atropisoméricos mediante olefinación asimétrica Pd (II)

Qi-Jun Yao1, Pei-Pei Xie1, Yong-Jie Wu1

  • 1Department of Chemistry, Zhejiang University, Hangzhou 310027, China.

Journal of the American Chemical Society
|October 8, 2020
PubMed
Resumen
Este resumen es generado por máquina.

Este estudio presenta un nuevo método para sintetizar anílidos quirales, una clase desafiante de compuestos quirales axialmente. La olefinación de C-H catalizada por Pd{\displaystyle Pd{\mathrm {II}} } obtiene altos rendimientos y una excelente estereoselectividad utilizando un ligando de aminoácidos naturales.

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Área de la Ciencia:

  • Química orgánica
  • Síntesis asimétrica
  • Compuestos quirales

Sus antecedentes:

  • Los anilidos atropisoméricos son compuestos quirales importantes con rotación restringida alrededor de un eje N-arilo.
  • La síntesis catalítica de anílidos quirales es un desafío debido a su libertad de rotación.

Objetivo del estudio:

  • Desarrollar una síntesis asimétrica catalítica eficiente para anílidos atropisoméricos.
  • Para explorar las aplicaciones de estos nuevos anilidos quirales.

Principales métodos:

  • La olefinación atroposelectiva del C-H catalizada por el paladio.
  • Se utiliza el ácido L-piroglutámico como ligando quiral.
  • Se emplearon estudios experimentales y computacionales (DFT) para comprender el mecanismo.

Principales resultados:

  • Se obtienen altos rendimientos (hasta el 99%) y una excelente enantioselectividad (hasta > 99% ee) para varios anilidos atropisoméricos.
  • Demostró la atropostabilidad de los anílidos sintetizados.
  • Identificó la distorsión del ligando en el paso de activación C-H como clave para la enantioselectividad.

Conclusiones:

  • Desarrolló una ruta directa y eficiente para desafiar a los anílidos atropisoméricos.
  • Mostró la utilidad de los anilidos sintetizados como ligandos quirales en otras transformaciones asimétricas.
  • Proporcionó conocimientos mecanicistas sobre la funcionalización C-H enantioselectiva.