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The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
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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.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
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In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
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Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
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Síntesis altamente enantioselectiva de Indazoles con un Centro Quaternario Quiral C3 utilizando la Catálisis CuH

Yuxuan Ye1, Ilia Kevlishvili2, Sheng Feng1

  • 1Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.

Journal of the American Chemical Society
|May 16, 2020
PubMed
Resumen
Este resumen es generado por máquina.

Ahora es posible lograr la alianza directa C3 de los indazoles, bloques de construcción farmacéuticos cruciales. Esta reacción catalizada por cobre crea valiosos indazoles C3-alilo con alta enantioselectividad, superando las limitaciones sintéticas anteriores.

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Área de la Ciencia:

  • Química orgánica
  • Química medicinal
  • Catálisis

Sus antecedentes:

  • Los 1H-indazoles sustituidos por C3 son andamios farmacéuticos vitales.
  • La funcionalización directa C3 de los indazoles sigue siendo sintéticamente difícil en comparación con las posiciones N1/N2.

Objetivo del estudio:

  • Desarrollar un método de alilación selectiva directa C3 para los 1H-indazoles.
  • Para sintetizar C3-alil 1H-indazoles enriquecidos enantioméricamente con estereocentros cuaternarios.

Principales métodos:

  • El hidruro de cobre (CuH) catalizó la alilación C3 de los 1H-N-benzoiloxiindazoles.
  • Cálculos de la teoría funcional de la densidad (DFT) para aclarar el mecanismo de reacción y la selectividad.

Principales resultados:

  • Síntesis eficiente de diversos C3-alilo 1H-indazoles con estereocentros cuaternarios.
  • Se obtienen altos niveles de enantioselectividad en la reacción de alilación.
  • Los cálculos de DFT revelaron un estado de transición tipo Zimmerman-Traxler que rige la enantioselectividad.

Conclusiones:

  • Se ha establecido una nueva y eficiente alilación selectiva C3 de los indazoles.
  • La reacción proporciona acceso a valiosos derivados quirales de indazol para aplicaciones farmacéuticas.
  • La comprensión del estado de transición aclara los determinantes de enantioselectividad para el diseño futuro del catalizador.