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Towards a Series of Chiral Primary Amines Bearing α-Amino Acid and Benzo[d]imidazole Pendants, and Their Application in Asymmetric Aldol Reactions

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F17%3A39902351" target="_blank" >RIV/00216275:25310/17:39902351 - isvavai.cz</a>

  • Result on the web

    <a href="https://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0036-1588107" target="_blank" >https://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0036-1588107</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1055/s-0036-1588107" target="_blank" >10.1055/s-0036-1588107</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    Towards a Series of Chiral Primary Amines Bearing α-Amino Acid and Benzo[d]imidazole Pendants, and Their Application in Asymmetric Aldol Reactions

  • Original language description

    A straightforward reaction path towards chiral primary amines bearing α-amino acid and benzo[d]imidazole pendants has been developed. Six starting essential α-amino acids were converted into the target chiral amines in a four-step synthesis. The prepared amines were screened as organocatalysts in the direct asymmetric aldol reaction between 4-nitrobenzaldehyde or isatin and acetone or cyclohexanone. The aldol adducts were obtained in good chemical yields, diastereoselectivity¬ up to 97:3 (reactions with cyclohexanone), and enantioselectivity up to 71% ee. Trifluoroacetic acid and benzoic acid proved to be the best cocatalysts for the aldol process on 4-nitrobenzaldehyde and isatin, respectively.

  • Czech name

  • Czech description

Classification

  • Type

    J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database

  • CEP classification

  • OECD FORD branch

    10401 - Organic chemistry

Result continuities

  • Project

  • Continuities

    S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Others

  • Publication year

    2017

  • Confidentiality

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

Data specific for result type

  • Name of the periodical

    Synthesis

  • ISSN

    0039-7881

  • e-ISSN

  • Volume of the periodical

    49

  • Issue of the periodical within the volume

    7

  • Country of publishing house

    DE - GERMANY

  • Number of pages

    10

  • Pages from-to

    1613-1622

  • UT code for WoS article

    000398467400018

  • EID of the result in the Scopus database