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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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...
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis01:07

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Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an alkylated β-keto acid.
Aldehydes and Ketones with Alcohols: Hemiacetal Formation01:19

Aldehydes and Ketones with Alcohols: Hemiacetal Formation

Similar to water, alcohols can add to the carbonyl carbon of the aldehydes and ketones. The addition of one molecule of alcohol to the carbonyl compound forms the hemiacetal or half acetal. As depicted below, in a hemiacetal, the carbon is directly linked to an OH and OR group.
Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones01:24

Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones

Acetals are formed by reacting two equivalents of alcohol with carbonyl compounds like aldehydes or ketones. Acetals are unaffected by bases, nucleophiles, oxidizing agents, and reducing agents. They serve as protecting groups for aldehydes and ketones. Acetals can be easily formed and also easily removed via mild acid hydrolysis.
In the presence of multiple functional groups, when selective reduction of one group over the other is desired, groups like aldehydes and ketones that form acetals...
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

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By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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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Published on: April 4, 2014

La transacetalización asimétrica catalítica de la transacetalización

Ilija Corić1, Sreekumar Vellalath, Benjamin List

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

Journal of the American Chemical Society
|June 10, 2010
PubMed
Resumen
Este resumen es generado por máquina.

Un nuevo método catalítico permite la transacetalización enantioselectiva utilizando TRIP, un ácido fosfórico quiral. Esta reacción proporciona una nueva ruta para la síntesis asimétrica de acetalos, creando un único centro estereogénico.

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Área de la Ciencia:

  • Química orgánica es la química orgánica.
  • Síntesis asimétrica de síntesis.

Sus antecedentes:

  • La transacetalización es una reacción clave en la síntesis orgánica.
  • El desarrollo de métodos enantioselectivos para la formación de acetal es crucial para acceder a las moléculas quirales.

Objetivo del estudio:

  • Desarrollar una reacción catalítica de transacetalización enantioselectiva.
  • Para utilizar ácidos fósforicos quirales como catalizadores para esta transformación.

Principales métodos:

  • El uso de TRIP (ácido fosfórico quiral) como catalizador.
  • Reaccionando con O,O-acetales bajo condiciones catalíticas.

Principales resultados:

  • TRIP demostró una alta eficiencia y enantioselectividad en la transacetalización.
  • La reacción produjo exitosamente acetalos con un solo centro estereogénico.

Conclusiones:

  • Se ha logrado una nueva transacetalización catalítica enantioselectiva.
  • El ácido fosfórico quiral TRIP es un catalizador eficaz para la síntesis asimétrica de acetal.