title: Investigation of chiral reactions: the structural detection of new hydrogenated isocinchona alkaloids from mixtures without isolation using electrospray ionization tandem mass spectrometry.
abstract: The reaction mixture for the hydrogenation of ethyl pyruvate on Pt-alumina catalyst modified with isocinchona alkaloids (alpha-ICN (I) and beta-ICN (II)) was studied by electrospray ionization tandem mass spectrometry (ESI-MS/MS). It was established that part of the chiral modifiers themselves are converted into ions of m/z 299, 305 and 309 in the course of chiral hydrogenation. The experimental data allowed the determination of the probable structure of the ions mentioned. According to ESI-MS/MS spectra the structure of the new cinchona alkaloids was assumed: tetrahydro-isocinchonines (III-VI), decahydro-isocinchonines (VII, VIII) and hydrogenated compounds of VII and VIII by scission of their C--N and C--O bonds (IX/1, IX/2, X). Fragmentation pathways are proposed for these new compounds.
authors.affiliation: Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary. bartok@chem.u-szeged.hu
authors.forename: Mihály
authors.initials: M
authors.lastname: Bartók
authors.forename: Zoltán
authors.initials: Z
authors.lastname: Kele
authors.forename: Mária
authors.initials: M
authors.lastname: Sutyinszki
authors.forename: Imre
authors.initials: I
authors.lastname: Bucsi
authors.forename: Károly
authors.initials: K
authors.lastname: Felföldi
mesh_terms: D002930:Cinchona Alkaloids / Q000737:chemistry*; D015394:Molecular Structure; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods*; D013237:Stereoisomerism
chemical_list: D002930:Cinchona Alkaloids