Ketone transformation as a pathway to inherently chiral rigidified calix[4]arenes
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F20%3A43920619" target="_blank" >RIV/60461373:22310/20:43920619 - isvavai.cz</a>
Result on the web
<a href="https://pubs.rsc.org/en/content/articlelanding/2020/CC/D0CC05352J#!divAbstract" target="_blank" >https://pubs.rsc.org/en/content/articlelanding/2020/CC/D0CC05352J#!divAbstract</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/d0cc05352j" target="_blank" >10.1039/d0cc05352j</a>
Alternative languages
Result language
angličtina
Original language name
Ketone transformation as a pathway to inherently chiral rigidified calix[4]arenes
Original language description
The preparation of inherently chiral rigidified calix[4]arenes with an intact cavity is a synthetic challenge due to the complicated synthesis of the starting compounds. Here, we report on a novel strategy for bridging the upper rim of calix[4]arenes consisting in carbonyl group formation and subsequent "extension" into a two-atom bridge using corresponding rearrangement reactions (Baeyer-Villiger, Beckmann). The resulting inherently chiral compounds are potentially applicable in the design of novel receptors. The complexation properties towards selected quaternary ammonium salts were studied by(1)H NMR titration. Unusual complexation stoichiometries can be observed depending on the enantiomeric purity (racemic mixtureversuspure enantiomers) of an amidic receptor 7 used.
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/GC18-08680J" target="_blank" >GC18-08680J: The synthesis and exploration of chromogenic and fluorogenic chiral calixarenes and related compounds</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2020
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Chemical Communications
ISSN
1359-7345
e-ISSN
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Volume of the periodical
56
Issue of the periodical within the volume
84
Country of publishing house
GB - UNITED KINGDOM
Number of pages
4
Pages from-to
12773-12776
UT code for WoS article
000580724600014
EID of the result in the Scopus database
2-s2.0-85094220420