Jove
Visualize
Contáctanos
JoVE
x logofacebook logolinkedin logoyoutube logo
ACERCA DE JoVE
Visión GeneralLiderazgoBlogCentro de Ayuda JoVE
AUTORES
Proceso de PublicaciónConsejo EditorialAlcance y PolíticasRevisión por ParesPreguntas FrecuentesEnviar
BIBLIOTECARIOS
TestimoniosSuscripcionesAccesoRecursosConsejo Asesor de BibliotecasPreguntas Frecuentes
INVESTIGACIÓN
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchivo
EDUCACIÓN
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualCentro de Recursos para ProfesoresSitio de Profesores
Términos y Condiciones de Uso
Política de Privacidad
Políticas

Videos de Conceptos Relacionados

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.4K
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...
3.4K
Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

3.1K
Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
3.1K
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

3.8K
Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
3.8K
Prochirality02:05

Prochirality

3.9K
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...
3.9K
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

4.1K
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...
4.1K
Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

4.0K
Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
4.0K

También podría leer

Artículos Relacionados

Artículos vinculados a este trabajo por autores compartidos, revista y gráfico de citas.

Ordenar por
Same author

Identification of 11α/β-hydroxy-12β-deoxysaxitoxin (12β-deoxyM2) in bivalve molluscs.

Journal of chromatography. B, Analytical technologies in the biomedical and life sciences·2026
Same author

Temporal orchestration of transcriptional and epigenomic programming underlying maternal embryonic diapause in a cricket model.

Communications biology·2026
Same author

Biosynthetic pathway of juvenile hormone III skipped bisepoxide in the stink bug Plautia stali (Hemiptera: Pentatomidae).

Journal of insect physiology·2026
Same author

Innervated superficial circumflex iliac artery perforator flap for refractory elbow ulcer with bone exposure in Werner syndrome: A case report.

JPRAS open·2026
Same author

Cooperative Chiral Induction in Aromatic <i>N</i>,<i>N</i>'-Dialkylated Urea Organocatalyst Enables Asymmetric Aza-Henry Reaction.

The Journal of organic chemistry·2026
Same author

Calcineurin-responsive zinc finger 1 (Crz1) contributes to stress tolerance and virulence in the pathogenic fungus <i>Trichosporon asahii</i>.

Infection and immunity·2026

Video Experimental Relacionado

Updated: Sep 9, 2025

Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

6.9K

Síntesis enantioselectiva a escala de gramo de rasagilina mediante reducción catalizada por ácido fosfórico quiral de

Hayate Ishizuka1, Toma Osawa1, Yuta Shimizu1

  • 1Department of Biotechnology and Life Science, Tokyo University of Agriculture and Technology, 2-24-16, Naka-cho, Koganei, Tokyo, 184-8588, Japan.

Chemistry, an Asian journal
|August 31, 2025
PubMed
Resumen
Este resumen es generado por máquina.

Se desarrolló una nueva vía de síntesis enantioselectiva para el mesilato de rasagilina utilizando la hidrogenación de transferencia asimétrica (ATH) de iminas cíclicas. Este método escalable proporciona altos rendimientos y enantioselectividad, ofreciendo una alternativa práctica para la síntesis de fármacos para la enfermedad de Parkinson.

Palabras clave:
Transferencia asimétrica de hidrógenoÁcido fosfórico quiralIminación cíclicaEl éster de HantzschRasagilina y sus derivados

Más Videos Relacionados

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

7.0K
Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
11:04

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine

Published on: June 13, 2022

3.1K

Videos de Experimentos Relacionados

Last Updated: Sep 9, 2025

Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

6.9K
Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

7.0K
Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
11:04

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine

Published on: June 13, 2022

3.1K

Área de la Ciencia:

  • Química orgánica
  • Química medicinal
  • Catálisis

Sus antecedentes:

  • El mesilato de rasagilina es un inhibidor clave de la monoamina oxidasa B para el tratamiento de la enfermedad de Parkinson.
  • Los métodos convencionales de síntesis para el mesilato de rasagilina son ineficientes y difíciles de escalar debido a la dependencia de la resolución óptica.
  • El desarrollo de vías de síntesis enantioselectivas es crucial para mejorar la fabricación de fármacos.

Objetivo del estudio:

  • Desarrollar una nueva, eficiente y escalable síntesis enantioselectiva de mesilato de rasagilina.
  • Para superar los desafíos asociados con la reducción de productos intermedios rígidos cíclicos.
  • Establecer un método ampliamente aplicable para la reducción asimétrica de las iminas cíclicas.

Principales métodos:

  • Hidrogenación asimétrica por transferencia (ATH) de un intermediario cíclico de propargilina.
  • Utilizó un catalizador de ácido fosfórico quiral junto con un éster de Hantzsch.
  • Escaló la reacción a niveles de gramos para evaluar la practicidad y la eficiencia.

Principales resultados:

  • Se obtienen altos rendimientos y una excelente enantioselectividad en la síntesis de aminas quirales.
  • Se ha sintetizado con éxito el mesilato de rasagilina con un exceso enantiomérico del 96%.
  • Se ha demostrado una amplia compatibilidad con el sustrato, lo que indica una utilidad general para los derivados de iminas cíclicas.

Conclusiones:

  • El método ATH desarrollado ofrece una alternativa práctica y escalable para sintetizar el mesilato de rasagilina.
  • Esta estrategia supera las limitaciones de las rutas de síntesis tradicionales para las aminas ópticamente activas.
  • La metodología tiene un potencial significativo para la síntesis de varios productos farmacéuticos que contienen aminas quirales.