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Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

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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...
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Preparation of Amines: Alkylation of Ammonia and Amines01:30

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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...
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Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction01:26

Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction

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α-Substituted ketones or aldehydes can be synthesized from enamines by the Stork enamine reaction, named after its pioneer Gilbert Stork. Enamines are useful synthetic intermediates where the lone pair on nitrogen is in conjugation with the C=C bond. They resemble enolate ions, as the resonance forms of both species have a nucleophilic α carbon.
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Amines to Amides: Acylation of Amines01:19

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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...
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Preparation of 1° Amines: Gabriel Synthesis01:28

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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...
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Structure of Amines

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The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’ carbon–carbon bond (154 pm). These aspects are...
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Síntesis diastereo y enantioselectiva de aminas homoalílicas con centros de carbono cuaternario

Jacob C Green1, Joseph M Zanghi1, Simon J Meek1

  • 1Department of Chemistry , The University of North Carolina at Chapel Hill , Chapel Hill , North Carolina 27599-3290 , United States.

Journal of the American Chemical Society
|January 15, 2020
PubMed
Resumen

Una nueva reacción catalizada por el cobre sintetiza eficientemente aminas quirales homoalílicas con carbonos cuaternarios. Este método utiliza reactivos fácilmente disponibles y proporciona altos rendimientos y estereoselectividad para valiosos intermedios sintéticos.

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Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • Metodología sintética

Sus antecedentes:

  • Las aminas homoalílicas quirales son bloques de construcción cruciales en la síntesis orgánica.
  • Los métodos eficientes para construir centros de carbono cuaternarios siguen siendo un desafío sintético.

Objetivo del estudio:

  • Desarrollar un nuevo método catalizado por el cobre para la síntesis enantioselectiva de aminas quirales homoalílicas.
  • Introducir un centro de carbono cuaternario y una porción de alquenilborón en una sola transformación.

Principales métodos:

  • Reacción catalizada por el cobre utilizando un ligando de fosforamidita.
  • Se utilizaron γ,γ alildiborones y iminas bencílicas estables en el banco.
  • Transmetación enantioselectiva formando especies de cobre alilico estabilizadas con boro.

Principales resultados:

  • Se ha logrado una síntesis enantio- y diastereoselectiva eficiente de los compuestos objetivo.
  • Se obtienen productos con un rendimiento de hasta el 82% con una alta relación diastereomérica (>20:1) y una relación enantiomérica (>99:1).
  • Demostró la utilidad sintética de los productos de 1-amino-3-alquenilboronato a través de varias transformaciones.

Conclusiones:

  • El método desarrollado catalizado por cobre proporciona una ruta poderosa a las aminas quirales homoalílicas complejas.
  • La reacción procede a través de un ciclo catalítico bien definido que involucra intermedios estereodeterminados.
  • Los productos resultantes sirven como versátiles sintetizadores para otras modificaciones químicas.