Synthesis of enantiomerically pure inherently chiral calix[4]arenes using the meta-substitution strategy
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F19%3A43919820" target="_blank" >RIV/60461373:22310/19:43919820 - isvavai.cz</a>
Result on the web
<a href="https://www.sciencedirect.com/science/article/pii/S0040403918314680?via%3Dihub" target="_blank" >https://www.sciencedirect.com/science/article/pii/S0040403918314680?via%3Dihub</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.tetlet.2018.12.026" target="_blank" >10.1016/j.tetlet.2018.12.026</a>
Alternative languages
Result language
angličtina
Original language name
Synthesis of enantiomerically pure inherently chiral calix[4]arenes using the meta-substitution strategy
Original language description
A meta-substituted aminocalix[4]arene 4 immobilized in the cone conformation was prepared via mercuration of the starting tetra-propoxy derivative, followed by nitrosation and reduction reactions. Acylation of the amino group by chiral amino acid residues ((S)-N-trifluoroacetyl-Ala or (S)-N-trifluoroacetyl-Phe) allowed for the preparation of diastereomeric amides that were separated by preparative TLC on silica gel. Subsequent cyclization under Bischler-Napieralski reaction conditions yielded calixarenes 7b and 7c bearing an oxazole moiety in the meta position instead of the expected upper rim-bridged compounds. The reaction sequence represents a straightforward approach towards enantiomerically pure inherently chiral calix[4]arene derivatives (without HPLC separation steps). The absolute configuration of the enantiomers were confirmed by single crystal structure determination (X-ray). © 2018 Elsevier Ltd
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
2019
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Tetrahedron Letters
ISSN
0040-4039
e-ISSN
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Volume of the periodical
60
Issue of the periodical within the volume
3
Country of publishing house
US - UNITED STATES
Number of pages
4
Pages from-to
260-263
UT code for WoS article
000456353000011
EID of the result in the Scopus database
2-s2.0-85058548281