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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

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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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Regioselectivity and Stereochemistry of Hydroboration02:36

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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
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Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

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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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ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

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All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
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Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

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In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
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Multifuncionalización enantioselectiva con carbinoides Rh

Yu Qian1, Jie Tang1, Xiaoyu Zhou2

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Journal of the American Chemical Society
|November 22, 2023
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Resumen
Este resumen es generado por máquina.

Este estudio introduce la primera trifuncionalización asimétrica utilizando carbinoides de rodio. Este nuevo método crea eficientemente moléculas complejas formando tres nuevos enlaces en un solo paso, produciendo diversos ésteres beta-amino con alta enantioselectividad.

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Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • Metodología sintética

Sus antecedentes:

  • La multifuncionalización es clave para la síntesis eficiente de moléculas complejas.
  • Las reacciones con carbinoides metálicos que muestran comportamiento de carbeno/carbocatión son limitadas.
  • El desarrollo de versiones enantioselectivas de estas reacciones es un desafío.

Objetivo del estudio:

  • Para presentar la primera reacción de trifuncionalización asimétrica utilizando carbinoides de rodio.
  • Para demostrar una nueva estrategia para la construcción de andamios moleculares complejos.
  • Para lograr altos rendimientos y enantioselectividad en la síntesis de ésteres beta-amino.

Principales métodos:

  • Utilizando carbinoides de rodio para la trifuncionalización.
  • El uso de una estrategia que implica la formación de dos ylidos de carbenos distintos.
  • Atrapar a un ylide con un imine para formar tres nuevos enlaces.

Principales resultados:

  • Desarrollo exitoso de la primera trifuncionalización asimétrica con carbinoides de rodio.
  • Demostración de la reacción del precursor carbinoide con dos nucleófilos y un electrófilo.
  • Alto rendimiento y excepcional enantioselectividad en la síntesis de diversos ésteres beta-amino.

Conclusiones:

  • Este trabajo establece un nuevo punto de referencia en la catálisis asimétrica.
  • El método desarrollado ofrece una herramienta poderosa para la síntesis divergente.
  • La estrategia permite la construcción eficiente y enantioselectiva de andamios valiosos de ésteres beta-amino.