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Synthesis of a Bolm's 2,2'-Bipyridine Ligand Analogue and Its Applications

Publikace na Přírodovědecká fakulta, Ústřední knihovna |
2018

Tento text není v aktuálním jazyce dostupný. Zobrazuje se verze "en".Abstrakt

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.