74927-72-3Relevant articles and documents
Chiral High-Pressure Liquid Chromatographic Stationary Phases. 3. General Resolution of Arylalkylcarbinols
Pirkle, William H.,Finn, John M.
, p. 2935 - 2938 (1981)
Enantiomers of arylalkylcarbinols (1) may be separated by chromatography upon a stationary phase comprised of chiral N-(3,5-dinitrobenzoyl)phenylglycine ionically bonded to γ-aminopropyl silanized silica.The order of elution of the enantiomers is related to the absolute configuration by a chiral recognition model.Hence, absolute configurations as well as enantiomeric purity can be conveniently determined on as little as nanogram quantities of carbinol.Alternatively, preparative separations can be performed upon the chiral phase, the scale being dictated by the column size.A convenient in situ method for preparation of efficient high-pressure liquid chromatography (HPLC) columns of this type is described.
COMPOSITIONS AND METHODS FOR CYCLOFRUCTANS AS SEPARATION AGENTS
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Page/Page column 48, (2010/12/31)
The present invention relates to derivatized cyclofructan compounds, compositions comprising derivatized cyclofructan compounds, and methods of using compositions comprising derivatized cyclofructan compounds for chromatographic separations of chemical species, including enantiomers. Said compositions may comprise a solid support and/or polymers comprising derivatized cyclofructan compounds.
Development of new HPLC chiral stationary phases based on native and derivatized cyclofructans
Sun, Ping,Wang, Chunlei,Breitbach, Zachary S.,Zhang, Ying,Armstrong, Daniel W.
experimental part, p. 10215 - 10226 (2010/05/01)
An unusual class of chiral selectors, cyclofructans, is introduced for the first time as bonded chiral stationary phases. Compared to native cyclofructans (CFs), which have rather limited capabilities as chiral selectors, aliphatic-and aromatic-functionalized CF6s possess unique and very different enantiomeric selectivities. Indeed, they are shown to separate a very broad range of racemic compounds. In particular, aliphatic-derivatized CF6s with a low substitution degree baseline separate all tested chiral primary amines. It appears that partial derivatization on the CF6 molecule disrupts the molecular internal hydrogen bonding, thereby making the core of the molecule more accessible. In contrast, highly aromaticfunctionalized CF6 stationary phases lose most of the enantioselective capabilities toward primary amines, however they gain broad selectivity for most other types of analytes. This class of stationary phases also demonstrates high "loadability" and therefore has great potential for preparative separations. The variations in enantiomeric selectivity often can be correlated with distinct structural features of the selector. The separations occur predominantly in the presence of organic solvents.
Continuous separation of racemic 3,5-dinitrobenzoyl-amino acids in a centrifugal contact separator with the aid of cinchona-based chiral host compounds
Hallett, Andrew J.,Kwant, Gerard J.,De Vries, Johannes G.
supporting information; experimental part, p. 2111 - 2120 (2009/09/30)
The resolution of racemates is mostly performed by crystallisation of diastereomeric salts. Direct physical separation could be much more efficient, but so far most concepts, with the exception of SMB, have proven to be non-scaleable. Here we report the f
Chiral permselectivity in nanoporous opal films surface-modified with chiral selector moieties
Cichelli, Julie,Zharov, Ilya
, p. 1870 - 1875 (2008/02/07)
The chiral permselectivity in thin opal films modified on the silica surface with chiral selector moieties was studied as a function of opal film geometry, supporting electrolyte concentration, solvent polarity, and chiral selector and linker structure. While opal film thickness, supporting electrolyte concentration and linker length and structure did not have a significant influence on the chiral permselectivity, the nanopore size, solvent polarity and selector structure had a pronounced effect. These observations are in agreement with the chiral selectivity mechanism in the opal films in which the permeating enantiomers are transported with different rates through the surface utilizing non-covalent interactions between the chiral permeant molecules and surface-bound chiral selectors. The chiral selectivity (transport rate ratio for S and R enantiomers) achieved in the present study was 4.5, which is one of the highest reported for chiral membranes. The Royal Society of Chemistry 2007.
Enantioselective hydrolysis of N-acylated α-amino esters at a biphasic interface: Tandem reaction kinetic resolution using a chiral complexing agent
Snyder, Seth E.,Pirkle, William H.
, p. 3283 - 3286 (2007/10/03)
equation presented Highly enantioselective hydrolytic kinetic resolutions of esters derived from N-acylated α-amino acids proceed rapidly at hydrocarbon/water interfaces in the presence of a proline-derived chiral selector. When performed in tandem with an enantioselective biphasic esterification reaction, esters of 100% enantiomeric excess are obtained.
