59543-81-6Relevant articles and documents
Chirality transfer in imidazolium camphorsulfonate ionic liquids through ion pairing effects
Schneiders, Karola,Boesmann, Andreas,Schulz, Peter S.,Wasserscheid, Peter
, p. 432 - 440 (2009)
The paper describes our studies on ion pair interactions in ionic liquids (IL) using an asymmetric hydrogenation reaction as probe. Three different ionic liquids carrying prochiral keto-functionalized cations were hydrogenated in the presence of their chiral, enantiomerically pure counter-ion using an achiral heterogeneous ruthenium catalyst. For the hydrogenation of N-(3′-oxobutyl) -N-methylimidazolium camphorsulfonate (2), N-(3′-oxobutyl)imidazolium camphorsulfonate (4) and N-(5′-oxohexyl)-N-methylimidazolium camphorsulfonate (6) we found a strong dependency of the enantiomeric excess (ee in the cation) on the polarity of the solvent, the concentration of the IL and the structure of the IL. The highest ee values of up to 94% were found for the hydrogenation of 2 in ethanol. Interestingly, we observed that the ee (and consequently the strength of ion pair interaction) had a pronounced maximum for a certain concentration of the IL in the solvent depending on the nature of the solvent and on the substrate. Remarkably, the concentration leading to the maximum ee could be rationalized by independent determination of the degree of dissociation which was obtained by a combination of diffusion-ordered NMR spectroscopy and conductivity measurements.
TiCl2(OTf)-SiO2: A solid stable lewis acid catalyst for Michael addition of α-Aminophosphonates, Amines, Indoles and Pyrrole
Firouzabadi, Habib,Iranpoor, Naser,Farahi, Soghra
, p. 317 - 323 (2018/02/06)
TiCl2(OTf)-SiO2 is simply prepared by immobilization of TiCl3(OTf) on silica gel surface and introduced as a non-hygroscopic Lewis acid catalyst for C-N and C-C bond formation via Michael addition reaction. A variety of structurally diverse nitrogen nucleophiles including α-aminophosphonates, aliphatic and aromatic amines and imidazole were evaluated as Michael donors. Friedel–Crafts alkylation of indoles and pyrrole was also investigated through Michael addition reaction in the presence of TiCl2(OTf)-SiO2 as a catalyst. The reactions were conducted at room temperature or 60 °C under solvent-free conditions and the desired Michael adducts were obtained in high to excellent yields.
Addition of azoles to methyl vinyl ketone by the Aza-Michael reaction
Hayotsyan,Khachatryan,Baltayan,Attaryan,Hasratyan
, p. 993 - 995 (2015/06/08)
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