title: Enantioselective separation of racemic secondary amines on a chiral crown ether-based liquid chromatography stationary phase.
abstract: The first general enantioselective separation of racemic secondary amines on a crown ether-based liquid chromatography chiral stationary phase (CSP) is presented. The CSP is based on (+)- or (-)-(18-crown-6)-2,3,11,12-tetracarboxylic acid covalently bonded to silica gel. A mobile phase containing methanol, acetonitrile, triethylamine and acetic acid was employed in these separations of secondary amines with crown ether CSPs. The separation mechanism is believed to be the secondary amine forming a complex which includes crown ether coordination and electrostatic interaction of the positively charged amine with a carboxylate anion of the immobilized crown ether.
authors.affiliation: Pharmacia Corporation, Skokie, IL 60077, USA.
authors.forename: Robert J
authors.initials: RJ
authors.lastname: Steffeck
authors.forename: Yury
authors.initials: Y
authors.lastname: Zelechonok
authors.forename: Kyung H
authors.initials: KH
authors.lastname: Gahm
mesh_terms: D000588:Amines / Q000737:chemistry / Q000302:isolation & purification*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D004988:Ethers, Cyclic / Q000737:chemistry*; D055672:Static Electricity; D013237:Stereoisomerism
chemical_list: D000588:Amines; D004988:Ethers, Cyclic