scholarly journals Helicity: A Non-Conventional Stereogenic Element for Designing Inherently Chiral Ionic Liquids for Electrochemical Enantiodifferentiation

Molecules ◽  
2021 ◽  
Vol 26 (2) ◽  
pp. 311
Author(s):  
Francesca Fontana ◽  
Greta Carminati ◽  
Benedetta Bertolotti ◽  
Patrizia Romana Mussini ◽  
Serena Arnaboldi ◽  
...  
Keyword(s):  
Ionic Liquids ◽  
Stationary Phase ◽  
Chiral Stationary Phase ◽  
Bioactive Molecules ◽  
Organic Salt ◽  
Preparative Hplc ◽  
Enantiomerically Pure ◽  
Chiral Ionic Liquids ◽  
Quaternary Salts ◽  
Inherently Chiral

Configurationally stable 5-aza[6]helicene (1) was envisaged as a promising scaffold for non-conventional ionic liquids (IL)s. It was prepared, purified, and separated into enantiomers by preparative HPLC on a chiral stationary phase. Enantiomerically pure quaternary salts of 1 with appropriate counterions were prepared and fully characterized. N-octyl-5-aza[6]helicenium bis triflimidate (2) was tested in very small quantities as a selector in achiral IL media to perform preliminary electrochemical enantiodifferentiation experiments on the antipodes of two different chiral probes. The new organic salt exhibited outstanding enantioselection performance with respect to these probes, thus opening the way to applications in the enantioselective electroanalysis of relevant bioactive molecules.

scholarly journals 2,12-Diaza[6]helicene: An Efficient Non-Conventional Stereogenic Scaffold for Enantioselective Electrochemical Interphases

Chemosensors ◽  
2021 ◽  
Vol 9 (8) ◽  
pp. 216
Author(s):  
Francesca Fontana ◽  
Benedetta Bertolotti ◽  
Sara Grecchi ◽  
Patrizia Romana Mussini ◽  
Laura Micheli ◽  
...  
Keyword(s):  
Ionic Liquids ◽  
Stationary Phase ◽  
Chiral Stationary Phase ◽  
Preparative Hplc ◽  
Additive Concentration ◽  
Oxidation Potentials ◽  
Inherently Chiral

The new configurationally stable, unsymmetrical 2,12-diaza[6]helicene was synthesized as a racemate and the enantiomers were separated in an enantiopure state by semi-preparative HPLC on chiral stationary phase. Under selected alkylation conditions it was possible to obtain both the enantiopure 2-N-mono- and di-N-ethyl quaternary iodides. Metathesis with bis(trifluoromethanesulfonyl)imide anion gave low-melting salts which were tested as inherently chiral additives to achiral ionic liquids for the electrochemical enantiodiscrimination of chiral organic probes in voltammetric experiments. Remarkable differences in the oxidation potentials of the enantiomers of two probes, a chiral ferrocenyl amine and an aminoacid, were achieved; the differences increase with increasing additive concentration and number of alkylated nitrogen atoms.

Pigments of Fungi. LXIII. Synthesis of (1S,3R)- and (1R,3S)-Austrocortilutein and the Enantiomeric Purity of Austrocortilutein in some Australian Dermocybe Toadstools

2000 ◽  
Vol 53 (1) ◽  
pp. 41 ◽  
Author(s):  
Catherine Elsworth ◽  
Melvyn Gill ◽  
Evelin Raudies ◽  
Abilio Ten
Keyword(s):  
Stationary Phase ◽  
Chiral Stationary Phase ◽  
Enantiomeric Purity ◽  
Diels Alder ◽  
Pure Form ◽  
Enantiomerically Pure ◽  
Naturally Occurring ◽  
First Time

The naturally occurring tetrahydroanthraquinones (1S,3R)- and (1R,3S)-austrocortilutein (1b) and (1d), respectively, are synthesized for the first time in enantiomerically pure form by Diels–Alder cycloaddition between the functionalized butadiene derivative (4) and the corresponding monochiral trans-1,3-dihydroxy-1,2,3,4- tetrahydro-5,8-naphthoquinone (5a) or (5b), themselves derived from citramalic acid. Separation of the four stereoisomeric austrocortiluteins by using h.p.l.c. over a chiral stationary phase reveals that the enantiomeric purity of the (1S,3S)- and (1R,3R)-quinones (1a) and (1c) varies from species to species whereas the (1S,3R)-isomer (1b) is, in the five cases examined, enantiomerically pure.

Synthesis and evaluation of l -phenylalanine ester-based chiral ionic liquids for GC stationary phase ability

2017 ◽  
Vol 237 ◽  
pp. 193-200 ◽  
Author(s):  
Irene W. Kimaru ◽  
Lydia Morris ◽  
Joanna Vassiliou ◽  
Nicole Savage
Keyword(s):  
Ionic Liquids ◽  
Stationary Phase ◽  
Chiral Ionic Liquids

Chiral drugs separation by a new antibiotics-based chiral stationary phase

2014 ◽  
Author(s):  
Chunye Liu ◽  
Yanqing Miao ◽  
Yihui Guo ◽  
Yinjuan An ◽  
Yunfang Li ◽  
...  
Keyword(s):  
Stationary Phase ◽  
Chiral Stationary Phase ◽  
Chiral Drugs ◽  
New Antibiotics

Advances in polymer materials as chiral stationary phase

2016 ◽  
Vol 34 (1) ◽  
pp. 34 ◽  
Author(s):  
Rongji DAI ◽  
Huiting WANG ◽  
Weiwei SUN ◽  
Yulin DENG ◽  
Fang LV ◽  
...  
Keyword(s):  
Stationary Phase ◽  
Chiral Stationary Phase ◽  
Polymer Materials

Indium Bromide-catalyzed Unprecedented Hydrogenolysis: A Novel One-Pot Synthesis of Per-O-Acetylated β-carboxymethyl O and S-glycosides

2020 ◽  
Vol 24 (8) ◽  
pp. 900-908
Author(s):  
Ram Naresh Yadav ◽  
Amrendra K Singh ◽  
Bimal Banik
Keyword(s):  
Asymmetric Synthesis ◽  
Chiral Auxiliary ◽  
Bioactive Molecules ◽  
One Pot ◽  
Enantiomerically Pure ◽  
Stereoselective Glycosylation ◽  
One Pot Synthesis ◽  
Wide Range

Numerous O (oxa)- and S (thia)-glycosyl esters and their analogous glycosyl acids have been accomplished through stereoselective glycosylation of various peracetylated bromo sugar with benzyl glycolate using InBr3 as a glycosyl promotor followed by in situ hydrogenolysis of resulting glycosyl ester. A tandem glycosylating and hydrogenolytic activity of InBr3 has been successfully investigated in a one-pot procedure. The resulting synthetically valuable and virtually unexplored class of β-CMGL (glycosyl acids) could serve as an excellent potential chiral auxiliary in the asymmetric synthesis of a wide range of enantiomerically pure medicinally prevalent β-lactams and other bioactive molecules of diverse medicinal interest.

Organocatalysis with Chiral Ionic Liquids

2014 ◽  
Vol 11 (2) ◽  
pp. 141-153 ◽  
Author(s):  
Karolina Zalewska ◽  
Luis C. Branco
Keyword(s):  
Ionic Liquids ◽  
Chiral Ionic Liquids
Sign in / Sign up

Export Citation Format

Share Document