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Synthesis of a Bolm's 2,2'-Bipyridine Ligand Analogue and Its Applications

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F18%3A10377755" target="_blank" >RIV/00216208:11310/18:10377755 - isvavai.cz</a>

  • Alternative codes found

    RIV/61388963:_____/18:00492366

  • Result on the web

    <a href="https://doi.org/10.1002/adsc.201800452" target="_blank" >https://doi.org/10.1002/adsc.201800452</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1002/adsc.201800452" target="_blank" >10.1002/adsc.201800452</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    Synthesis of a Bolm's 2,2'-Bipyridine Ligand Analogue and Its Applications

  • Original language description

    A new method of synthesis of an analogue of Bolm&apos;s 2,2&apos;-bipyridine ligand based on the catalytic [2+2+2] cyclotrimerization of 1-halodiynes with nitriles was developed. Crucial step of the whole synthesis turned out to be homodimerization of a substituted 2-bromopyridine to the corresponding bipyridine, that was studied and optimized. The newly prepared bipyridine (S,S)-2 was then tested as a chiral ligand in metal-catalyzed enantioselective reactions. Out of the studied reactions the most promising results were obtained in epoxide ring opening (82% yield, 98%ee) and Mukaiyama aldol reaction (&gt;96% yield, 99/1dr, 92%ee). In the case of Mukaiyama-aldol reaction as well as in the Michael addition, novel ligand 2 proved its robustness compared to Bolm&apos;s ligand as it was less sensitive to the purity of used reagents.

  • 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

    Result was created during the realization of more than one project. More information in the Projects tab.

  • Continuities

    P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Others

  • Publication year

    2018

  • Confidentiality

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

Data specific for result type

  • Name of the periodical

    Advanced Synthesis and Catalysis

  • ISSN

    1615-4150

  • e-ISSN

  • Volume of the periodical

    360

  • Issue of the periodical within the volume

    15

  • Country of publishing house

    DE - GERMANY

  • Number of pages

    10

  • Pages from-to

    2869-2878

  • UT code for WoS article

    000440815900012

  • EID of the result in the Scopus database

    2-s2.0-85051112556