Počet záznamů: 1
Synthesis of a Bolm's 2,2 '-Bipyridine Ligand Analogue and Its Applications
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SYSNO ASEP 0492366 Druh ASEP J - Článek v odborném periodiku Zařazení RIV J - Článek v odborném periodiku Poddruh J Článek ve WOS Název Synthesis of a Bolm's 2,2 '-Bipyridine Ligand Analogue and Its Applications Tvůrce(i) Bednářová, E. (CZ)
Dračínský, Martin (UOCHB-X) RID, ORCID
Malatinec, Š. (CZ)
Císařová, I. (CZ)
Lamaty, F. (FR)
Kotora, M. (CZ)Zdroj.dok. Advanced Synthesis & Catalysis. - : Wiley - ISSN 1615-4150
Roč. 360, č. 15 (2018), s. 2869-2878Poč.str. 10 s. Jazyk dok. eng - angličtina Země vyd. DE - Německo Klíč. slova catalysis ; enantioselective synthesis ; cyclotrimerization ; bipyridines ; chiral ligands Vědní obor RIV CC - Organická chemie Obor OECD Organic chemistry CEP LO1304 GA MŠMT - Ministerstvo školství, mládeže a tělovýchovy Institucionální podpora UOCHB-X - RVO:61388963 UT WOS 000440815900012 EID SCOPUS 85051112556 DOI 10.1002/adsc.201800452 Anotace 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. Pracoviště Ústav organické chemie a biochemie Kontakt asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Rok sběru 2019
Počet záznamů: 1