Organocatalyzed Asymmetric Henry Reaction of Alpha-Trifluorinated Acetophenones

Kód výsledku v IS VaVaI

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Výsledek na webu

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DOI - Digital Object Identifier

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Jazyk výsledku

angličtina

Název v původním jazyce

Organocatalyzed Asymmetric Henry Reaction of Alpha-Trifluorinated Acetophenones

Popis výsledku v původním jazyce

The syntheses of tetra-substituted chiral carbon-based stereocenters are, in general, demanding tasks in asymmetric synthesis. The chiral tertiary alcohols bearing an ?-CF3 group represent the interesting targets in medicinal chemistry because this functional group can considerably affect the pharmacokinetic properties of the target molecule by increasing its lipophilicity.Such substances can be effectively prepared by the asymmetric nitroaldol reaction. However the use of ketones as substrates for the asymmetric organocatalyzed Henry reaction is somewhat limited and underexplored in comparison with aldehydes, mostly due to their lower reactivity in nitro-aldolizations. Therefore we have concentrated on the screening of a large series of chiral non-racemic urea, thiourea, and squaramide organocatalysts on this type of transformation and a novel organocatalytic process has been successfully developed. This synthetic approach was subsequently applied to the total syntheses of diastereopure CB1-receptor inverse agonists as potential anorectic agents

Název v anglickém jazyce

Organocatalyzed Asymmetric Henry Reaction of Alpha-Trifluorinated Acetophenones

Popis výsledku anglicky

The syntheses of tetra-substituted chiral carbon-based stereocenters are, in general, demanding tasks in asymmetric synthesis. The chiral tertiary alcohols bearing an ?-CF3 group represent the interesting targets in medicinal chemistry because this functional group can considerably affect the pharmacokinetic properties of the target molecule by increasing its lipophilicity.Such substances can be effectively prepared by the asymmetric nitroaldol reaction. However the use of ketones as substrates for the asymmetric organocatalyzed Henry reaction is somewhat limited and underexplored in comparison with aldehydes, mostly due to their lower reactivity in nitro-aldolizations. Therefore we have concentrated on the screening of a large series of chiral non-racemic urea, thiourea, and squaramide organocatalysts on this type of transformation and a novel organocatalytic process has been successfully developed. This synthetic approach was subsequently applied to the total syntheses of diastereopure CB1-receptor inverse agonists as potential anorectic agents

Druh

O - Ostatní výsledky

CEP obor

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OECD FORD obor

30107 - Medicinal chemistry

Projekt

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Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2018

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů