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 - Journal Article
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
Institutional support: RVO:68378271
Keywords : N-oxides * N,N'-dioxides * cyclotrimerization * catalysis * silicon compounds * enantioselective synthesis
OECD category: Condensed matter physics (including formerly solid state physics, supercond.)
Impact factor: 1.349, year: 2019
Method of publishing: Limited access
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.

Permanent Link: http://hdl.handle.net/11104/0303995