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The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
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Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
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In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
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The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...
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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
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If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
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Una bromolactonización enantiodivergente controlada por catalizador

Yuk-Cheung Chan1, Xinyan Wang1, Ying-Pong Lam1

  • 1Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Shatin, NT, Hong Kong, China.

Journal of the American Chemical Society
|August 5, 2021
PubMed
Resumen
Este resumen es generado por máquina.

Este estudio introduce un nuevo método controlado por catalizador para la bromolactonización asimétrica de ácidos olefínicos. Un simple cambio en la estructura del catalizador invierte completamente el resultado estereocímico, produciendo lactonas enantioméricamente puras.

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Área de la Ciencia:

  • Química orgánica
  • Catálisis asimétrica
  • Metodología sintética

Sus antecedentes:

  • La síntesis enantioselectiva es crucial para los productos farmacéuticos y agroquímicos.
  • Desarrollar catalizadores que controlen la estereoquímica es un desafío clave.
  • La bromolactonización ofrece una vía para obtener valiosos productos de lactona.

Objetivo del estudio:

  • Desarrollar una bromolactonización enantidivergente controlada por catalizador de ácidos olefínicos.
  • Investigar el efecto de la estructura del catalizador en el resultado estereoquímico.
  • Para aclarar el mecanismo de reacción.

Principales métodos:

  • Se han utilizado catalizadores de aminoamidas derivados de la quinina.
  • Se ha realizado la bromolactonización enantiodivergente de ácidos olefínicos.
  • Estudios mecanicistas realizados, incluidos experimentos químicos y cálculos de DFT.

Principales resultados:

  • Se ha logrado una síntesis enantidivergente de lactonas controlada por catalizadores.
  • Demostró un cambio completo en la inducción asimétrica mediante la alteración de los sustituyentes del catalizador.
  • Se obtienen las lactonas deseadas con buena enantioselectividad y rendimiento.

Conclusiones:

  • Los efectos estéricos y electrónicos de los sustituyentes del catalizador influyen significativamente en el mecanismo de reacción.
  • Este trabajo proporciona un método versátil para acceder a las lactonas enantioméricamente enriquecidas.
  • El diseño del catalizador es crítico para controlar la estereoquímica en la síntesis orgánica.