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Videos de Conceptos Relacionados

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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Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

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Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
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α-Alkylation of Ketones via Enolate Ions01:10

α-Alkylation of Ketones via Enolate Ions

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Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
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[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement

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The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
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Reactivity of Enols01:18

Reactivity of Enols

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Enols are a class of compounds where a hydroxyl group is attached to a carbon–carbon double bond, which implies that it is a vinyl alcohol. A carbonyl compound with an α hydrogen undergoes keto–enol tautomerism and remains in equilibrium with its tautomer, the enol form. Usually, the keto tautomer is present in a higher concentration than the enol tautomer due to the higher bond energy of C=O compared to C=C. Moreover, the direction of the keto–enol equilibrium is...
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Preparation of Epoxides03:00

Preparation of Epoxides

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Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
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Sustitución alilica enantioselectiva catalizada por iridio de los silanos de enol a partir de ésteres y amidas

Ming Chen1, John F Hartwig1

  • 1Department of Chemistry, University of California , Berkeley, California 94720, United States.

Journal of the American Chemical Society
|October 7, 2015
PubMed
Resumen

Los silanos de enol, conocidos por las reacciones de Diels-Alder, son ahora nucleófilos efectivos en las sustituciones alilicas catalizadas por iridio. Este nuevo método proporciona altos rendimientos y enantioselectividades para productos aliados, con aplicaciones en la síntesis de fármacos.

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Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • Metodología sintética

Sus antecedentes:

  • Los enol silanos son dienos establecidos en las reacciones de Diels-Alder.
  • Su reactividad nucleofílica en reacciones catalizadas por metales de transición es menos explorada.

Objetivo del estudio:

  • Investigar la reactividad de los enol silanos como nucleófilos en la sustitución alilica enantioselectiva catalizada por iridio.
  • Desarrollar una nueva vía sintética para compuestos aliados.

Principales métodos:

  • Se utilizan ésteres vinílogos y amidas como nucleófilos de enol silano.
  • Se utiliza la catálisis del iridio con carbonatos alilicos como electrófilos.
  • Se ha investigado el papel de los aditivos (KF, alcóxidos) y los mecanismos de reacción.

Principales resultados:

  • Se obtienen buenos rendimientos y altas enantioselectividades para los productos aliados.
  • Demostró excelentes proporciones de ramificación a linealidad en los productos de sustitución.
  • Los estudios mecánicos revelaron el papel del aditivo en la activación del catalizador y el papel del anión carbonato en la activación del nucleófilo.

Conclusiones:

  • Los silanos de enol son nucleófilos versátiles en la sustitución alilica enantioselectiva catalizada por Ir.
  • El método desarrollado ofrece una herramienta poderosa para la construcción de moléculas orgánicas complejas.
  • La utilidad sintética fue validada a través de la síntesis del fármaco anti-muscarínico, fesoterodina.