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's 2,2'-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 (>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's ligand as it was less sensitive to the purity of used reagents.
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
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
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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