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
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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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
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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