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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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Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...
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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

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The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
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Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
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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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By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
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Una ciclización general catalítica asimétrica de Prins

Luping Liu1, Philip S J Kaib1, Aurélien Tap1

  • 1Max-Planck-Institut für Kohlenforschung , Kaiser Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany.

Journal of the American Chemical Society
|August 23, 2016
PubMed
Resumen

Los nuevos ácidos de imino-imidodifosfato (iIDP) de Brønsted permiten la ciclización asimétrica de Prins. Este eficiente método catalítico produce tetrahidropiranos funcionalizados, valiosos para sintetizar fragancias como el óxido de rosa.

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Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • Síntesis asimétrica

Sus antecedentes:

  • La ciclización de Prins es una reacción clave para la formación de estructuras tetrahidropiranas.
  • El desarrollo de métodos eficientes y enantioselectivos para esta transformación sigue siendo un desafío importante en la síntesis orgánica.

Objetivo del estudio:

  • Introducir una nueva clase de ácidos de Brønsted confinados de imino-imidodifosfato (iIDP).
  • Para utilizar estos catalizadores para la ciclización asimétrica de Prins de los aldehídos.

Principales métodos:

  • Utilizando ácidos Brønsted de imino-imidodifosfato confinado (iIDP) como catalizadores.
  • Reaccionando con aldehídos alifáticos y aromáticos bajo condiciones catalíticas para promover la ciclización de Prins.
  • Análisis de los productos de reacción para el rendimiento, la regioselectividad y la enantioselectividad.

Principales resultados:

  • Se obtienen buenos a excelentes rendimientos de diversos 4-metilenetetrahidropiranos funcionalizados.
  • Se han demostrado buenas o excelentes selectividades regionales y enantioficiales en los productos de ciclización.
  • Aplicó con éxito los catalizadores iIDP a la síntesis de compuestos de fragancia, incluidos el óxido de rosa y doremox.

Conclusiones:

  • Los ácidos de Brønsted desarrollados por iIDP representan una nueva clase de catalizadores eficaces para la ciclización asimétrica de Prins.
  • Esta metodología ofrece una vía enantioselectiva eficiente y escalable para obtener valiosos derivados de tetrahidropirano.
  • El sistema catalítico es aplicable a la síntesis de moléculas de fragancia importantes.