Noguchi, Hiroki;Takafuji, Makoto;Maurizot, Victor;Huc, Ivan;Ihara, Hirotaka published 《Chiral separation by a terminal chirality triggered P-helical quinoline oligoamide foldamer》. The research results were published in《Journal of Chromatography A》 in 2016.Product Details of 39637-74-6 The article conveys some information:
A P-helical quinoline oligoamide foldamer was grafted on silica and applied as an HPLC stationary phase for chiral separation The P-handedness of the quinoline oligoamide foldamer was induced by a (1S)-camphanyl group, which was introduced at the N-terminus of a tetrameric quinoline oligoamide foldamer (Cmp-Q4). To immobilize the foldamer on porous silica particles, a trimethoxysilyl group was introduced at the opposing end of the foldamer. Elemental anal. indicated that the amount of foldamer on the silica surface was 0.57 μmol/m2. CD and vibrational CD spectra of Cmp-Q4 and Cmp-Q4-immobilized silica (Sil-Q4-Cmp) suggested that the helical structure of Cmp-Q4 was altered on the silica surface while retaining a chiral structure. The chiral recognition ability of Sil-Q4-Cmp was evaluated with various aromatic enantiomers. Sil-Q4-Cmp showed enantio-selectivity for axially chiral mols. (e.g., αTrigger’s base = 1.26 and αBinaphthol = 1.07). Sil-Q4-Cmp showed remarkable recognition of helical octameric quinoline oligoamides with isobutoxy and triethylene glycol side chains (α 10.35and 14.98, resp.). In contrast, an (1S)-camphanyl group-immobilized porous silica showed no chiral recognition for any enantiomers tested. To elucidate the chiral separation mechanism of Sil-Q4-Cmp, thermodn. parameters were calculated using van’t Hoff plots. HPLC results and thermodn. parameters suggested that the chiral recognition of Sil-Q4-Cmp is based on the helical structure of Cmp-Q4 and other thermally dependent interactions such as hydrophobic effects associated with aromatic stacking. This work represents the 1st known application of aromatic foldamers in chiral separation The experimental procedure involved many compounds, such as (1S)-4,7,7-Trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl chloride(Chunks or pellets) (cas: 39637-74-6) .
(1S)-4,7,7-Trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl chloride(Chunks or pellets) (cas: 39637-74-6 Product Details of 39637-74-6) is a chiral derivatizing agent. It can be prepared by reacting (-)-(1S,4R)-camphanic acid with thionyl chloride.
Reference:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics