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Organocatalyzed Asymmetric Henry Reaction of Alpha-Trifluorinated Acetophenones

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F62157124%3A16370%2F18%3A43877162" target="_blank" >RIV/62157124:16370/18:43877162 - isvavai.cz</a>

  • Result on the web

  • DOI - Digital Object Identifier

Alternative languages

  • Result language

    angličtina

  • Original language name

    Organocatalyzed Asymmetric Henry Reaction of Alpha-Trifluorinated Acetophenones

  • Original language description

    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

  • Czech name

  • Czech description

Classification

  • Type

    O - Miscellaneous

  • CEP classification

  • OECD FORD branch

    30107 - Medicinal chemistry

Result continuities

  • Project

  • Continuities

    I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Others

  • Publication year

    2018

  • Confidentiality

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