Synthesis of new bipyridine N,N.sup.,./sup.-dioxides and their application in asymmetric allylation of benzaldehyde and aldol addition to acetophenone

0518983 - FZÚ 2020 RIV AT eng J - Článek v odborném periodiku
Bednářová, E. - Nečas, D. - Císarová, I. - Dušek, Michal - Lamaty, F. - Kotora, M.
Synthesis of new bipyridine N,N^,-dioxides and their application in asymmetric allylation of benzaldehyde and aldol addition to acetophenone.
Monatshefte fur Chemie. Roč. 150, č. 1 (2019), s. 29-48. ISSN 0026-9247. E-ISSN 1434-4475
Institucionální podpora: RVO:68378271
Klíčová slova: N-oxides * N,N'-dioxides * cyclotrimerization * catalysis * silicon compounds * enantioselective synthesis
Obor OECD: Condensed matter physics (including formerly solid state physics, supercond.)
Impakt faktor: 1.349, rok: 2019
Způsob publikování: Omezený přístup
https://doi.org/10.1007/s00706-018-2289-5

Chiral pyridine N-oxides and bipyridine N,N´-dioxides are an important class of heteroaromatic compounds with interesting chemical properties. Polarization of the N–O bond results in their electron-donation activity and makes them rather strong Lewis bases, which are able to activate Lewis acids such as trichlorosilanes. Therefore, they can catalyze a number of various reactions such as allylation and crotylation of aldehydes, aldol reactions, ring-opening of epoxides, and cyanosilylation of ketones and imides. Due to the general high interest in the development of new Lewis basic chiral organocatalysts, synthetic approaches providing new chiral compounds possessing the pyridine N-oxide moiety are desirable.

Trvalý link: http://hdl.handle.net/11104/0303995