Enantioselective synthesis of ammonium cations was written by Walsh, Mark P.;Phelps, Joseph M.;Lennon, Marc E.;Yufit, Dmitry S.;Kitching, Matthew O.. And the article was included in Nature (London, United Kingdom) in 2021.Reference of 69221-14-3 This article mentions the following:
Here showed that control of the chirality of ammonium cations was easily achieved through a supramol. recognition process. By combining enantioselective ammonium recognition mediated by 1,1′-bi-2-naphthol scaffolds with conditions that allow the nitrogen stereocentre to racemize, chiral ammonium cations could be produced in excellent yields and selectivities. Mechanistic investigations demonstrate that, through a combination of solution and solid-phase recognition, a thermodynamically driven adductive crystallization process was responsible for the observed selectivity. Distinct from processes based on dynamic and kinetic resolution, which were under kinetic control, this allows for increased selectivity over time by a self-corrective process. The importance of nitrogen stereocentres could be revealed through a stereoselective supramol. recognition, which was not possible with naturally occurring pseudoenantiomeric Cinchona alkaloids. In the experiment, the researchers used many compounds, for example, (1S,2R,4S,5R)-1-Benzyl-2-(hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium chloride (cas: 69221-14-3Reference of 69221-14-3).
(1S,2R,4S,5R)-1-Benzyl-2-(hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium chloride (cas: 69221-14-3) belongs to quinuclidine derivatives. Quinuclidine exists in a number of naturally occurring compounds, biologically active agents, and privileged catalysts and ligands for asymmetric catalysis. As a ligand, quinuclidine is useful in the studies of OsO4-catalyzed dihydroxylation of olefins. It plays an important role in the formation of onium salts used testing of PAC-antagonist activity.Reference of 69221-14-3
Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider