Video Experimental Relacionado
Updated: Jan 31, 2026
06:46
Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
7.9K
Hidroaminación asimétrica catalizada por el rodio de aminas aliloicas
Evan P Vanable1, Jennifer L Kennemur1, Leo A Joyce2
1Department of Chemistry , University of Illinois at Urbana-Champaign , 600 S. Mathews , Urbana , Illinois 61801 , United States.
Journal of the American Chemical Society
|January 8, 2019
Resumen
Este estudio introduce una hidroaminación enantioselectiva catalizada por Rh de las alilaminas, dando lugar a 1,2-diaminas enantioenriquecidas de alta selectividad. El método sintetiza eficientemente compuestos químicos valiosos, incluidos los intermedios farmacéuticos.
Área de la Ciencia:
- Química orgánica
- Catálisis
- Síntesis asimétrica
Sus antecedentes:
- Las 1,2-diaminas son bloques de construcción cruciales en los productos farmacéuticos y la síntesis orgánica.
- El desarrollo de métodos eficientes y enantioselectivos para su síntesis sigue siendo un desafío importante.
Objetivo del estudio:
- Para reportar una nueva hidroaminación enantioselectiva catalizada por el Rh de las alilaminas.
- Demostrar la amplia aplicabilidad de la metodología desarrollada.
Principales métodos:
- Utilizando un ligando quiral de tipo BIPHEP para la hidroaminación catalizada por el rodio.
- Empleando varias alilaminas con diversos nucleófilos y grupos de dirección de aminas.
Principales resultados:
- Se obtienen buenos rendimientos y excelentes enantioselectividades para la formación de 1,2-diaminas enriquecidas con enantio.
- Compatibilidad demostrada con una amplia gama de sustratos, incluidos los con motivos desprotegibles.
- Aplicó con éxito la metodología para la síntesis rápida de 2-metil-moclobemida.
Conclusiones:
- La hidroaminación catalizada por Rh desarrollada ofrece una ruta eficiente a las valiosas enantioenriquecidas de 1,2-diaminas.
- La versatilidad de la metodología la hace aplicable para la síntesis de moléculas complejas e intermedios farmacéuticos.
Videos de Conceptos Relacionados
01:11Rotation of Asymmetric Top
1.5K
By definition, a spherically symmetric body has the same moment of inertia about any axis passing through its center of mass. This situation changes if there is no spherical symmetry. Since most rigid bodies are not spherically symmetric, these require special treatment.
The relationship between the angular momentum of any rigid body and its angular velocity, both of which are vectors, involves the moment of inertia. The moment of inertia is a scalar quantity only for spherically symmetric...
The relationship between the angular momentum of any rigid body and its angular velocity, both of which are vectors, involves the moment of inertia. The moment of inertia is a scalar quantity only for spherically symmetric...
1.5K
01:35Asymmetric Lipid Bilayer
9.8K
Biological membranes show uneven distribution of different types of lipids in the inner and outer layers, resulting in transverse asymmetric membranes. The treatment of the erythrocyte membrane with the enzyme phospholipase confirmed the asymmetric nature of the lipid bilayer. The enzyme hydrolyzes lipids into fatty acids and hydrophilic groups. The phospholipase acts only on the outer layer of the membrane, while the inner layer remains intact. The phospholipase treatment resulted in 80%...
9.8K
01:19Amines to Amides: Acylation of Amines
3.5K
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
3.5K
01:30Preparation of Amines: Alkylation of Ammonia and Amines
4.7K
Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
4.7K
01:27π Molecular Orbitals of the Allyl Radical
4.5K
Allyl radicals are three-carbon conjugated systems. They are readily formed as intermediates in halogenation reactions of alkenes involving the addition of halogen to the allylic carbon instead of the double bond. As seen in allyl cations and anions, each of the three sp2-hybridized carbon atoms in allyl radicals has an unhybridized p orbital. These orbitals combine to give three π molecular orbitals.
The allyl systems have identical molecular orbitals but differ in the number of π electrons....
The allyl systems have identical molecular orbitals but differ in the number of π electrons....
4.5K
01:31Radical Substitution: Allylic Chlorination
3.2K
Typically, when alkenes react with halogens at low temperatures, an addition reaction occurs. However, upon increasing the temperature or under reaction conditions that form radicals, providing a low but steady concentration of halogen radicals, allylic substitution reaction is favored. This is because allylic hydrogens are very reactive as the formed intermediate is resonance stabilized. For example, when propene is treated with chlorine in the gas phase at 400 °C, it undergoes allylic...
3.2K