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Asymmetric Synthesis of Diastereo- and Enantiopure Bioxahelicene 2,2'-Bipyridines

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F18%3A00495682" target="_blank" >RIV/61388963:_____/18:00495682 - isvavai.cz</a>

  • Result on the web

    <a href="http://dx.doi.org/10.1002/ejoc.201800541" target="_blank" >http://dx.doi.org/10.1002/ejoc.201800541</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1002/ejoc.201800541" target="_blank" >10.1002/ejoc.201800541</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    Asymmetric Synthesis of Diastereo- and Enantiopure Bioxahelicene 2,2'-Bipyridines

  • Original language description

    A versatile asymmetric synthesis of five C2 symmetric enantio- and diastereopure bioxa[5]- and bioxa[6]helicene 2,2'-bipyridines was developed. It relied either on a double intramolecular [2+2+2] cycloisomerization of dicyanotetrayne (forming simultaneously the 2,2'-bipyridine unit and biazaoxahelicene backbone) or one-pot/sequential intramolecular [2+2+2] cycloisomerization of triyne accompanied by an intermolecular haloazaoxahelicene reductive homocoupling. We reached an effective central-to-helical-to-axial chirality transfer that was controlled by the 1,3-allylic-type strain and sterically constricted atropoisomerization of the embedded 2,2'-bipyridine unit. The chiroptical properties of the bioxahelicene 2,2'-bipyridines were studied along with their fluorescence properties.

  • 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

    <a href="/en/project/GA16-08294S" target="_blank" >GA16-08294S: Giant nonplanar aromatics: The quest for new functional materials</a><br>

  • 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

    European Journal of Organic Chemistry

  • ISSN

    1434-193X

  • e-ISSN

  • Volume of the periodical

    2018

  • Issue of the periodical within the volume

    37

  • Country of publishing house

    DE - GERMANY

  • Number of pages

    15

  • Pages from-to

    5164-5178

  • UT code for WoS article

    000446662900011

  • EID of the result in the Scopus database

    2-s2.0-85052789173