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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 conversion of allylic alcohols into epoxides using the chiral catalyst was discovered by K. Barry Sharpless and is known as Sharpless epoxidation. The use of a chiral catalyst enables the formation of one enantiomer of the product in excess. This chiral catalyst is mainly a chiral complex of titanium tetraisopropoxide and tartrate ester (specific stereoisomer). The stereoisomer used in the chiral catalyst dictates the formation of the enantiomer of the product. In other words, the use of...
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Introduction
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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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Piridina enantioselectiva catalítica N - Oxidación

Sheng-Ying Hsieh1, Yu Tang1, Simone Crotti1

  • 1Department of Chemistry , Yale University , New Haven , Connecticut 06520-8107 , United States.

Journal of the American Chemical Society
|October 29, 2019
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Resumen

Este estudio introduce un nuevo método catalítico para la N-oxidación enantioselectiva de las piridinas utilizando péptidos a base de ácido aspártico. Este enfoque biomimético logra una alta inducción asimétrica, creando valiosos marcos quirales de piridina.

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Área de la Ciencia:

  • Química orgánica
  • Catálisis asimétrica
  • Química medicinal

Sus antecedentes:

  • Los derivados de piridina quiral son componentes esenciales de los productos farmacéuticos.
  • El desarrollo de métodos eficientes para la síntesis asimétrica de N-heterociclos sigue siendo un desafío importante.

Objetivo del estudio:

  • Desarrollar un sistema catalítico inspirado en las biomoléculas para la N-oxidación enantioselectiva de las piridinas sustituidas.
  • Demostrar la utilidad de este método para sintetizar marcos quirales de piridina y su aplicabilidad a andamios similares a fármacos.

Principales métodos:

  • Se utilizan péptidos que contienen ácido aspártico para catalizar la N-oxidación enantioselectiva.
  • Se utiliza un ciclo catalítico que implica el traslado de la cadena lateral de aspartilo entre las formas ácida libre y peracida.
  • Se aplicó el método para desimetrizar sustratos de bis (pyridine) y funcionalizar los óxidos de N resultantes.

Principales resultados:

  • Se han logrado altos niveles de inducción asimétrica en la N-oxidación de las piridinas.
  • Se ha demostrado con éxito la desimetrización de sustratos de piridina con centros pro-esteroígenos remotos.
  • Se demostró la aplicabilidad del método a los andamios de la loratadina y la vareniclina y a las 1,4-pirazinas.

Conclusiones:

  • El sistema catalítico desarrollado proporciona una entrada nueva y eficiente en los marcos quirales de piridina.
  • El enfoque es versátil, aplicable a diversos entornos quirales y a los N-heterociclos relacionados.
  • Este método es prometedor para la síntesis de moléculas quirales complejas en química medicinal.