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Determination of Enantiomeric Purity and Absolute Configuration of β‐Lactams by High‐Performance Liquid Chromatography on Chiral Columns
Author(s) -
Lee ChihShone,
Chen HsiuHo
Publication year - 1994
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.199400026
Subject(s) - chemistry , enantiomer , chiral derivatizing agent , chiral column chromatography , imine , absolute configuration , chromatography , elution , amide , high performance liquid chromatography , enantiomeric excess , resolution (logic) , aryl , amino acid , organic chemistry , enantioselective synthesis , catalysis , alkyl , artificial intelligence , computer science , biochemistry
Enantiomers of β‐lactams bearing aryl, furyl or styryl substituents in the 4‐position were chromatographically separated by means of high‐performance liquid chromatography on chiral column packed with amino acid‐derived chiral stationary phase. Separation factors are generally modest. To improve further the resolution of enantiomers, the rings of these β‐lactams were opened with octanol in acidic conditions and converted into N‐3,5‐ dinitrobenzoyl ester derivatives of the resulting β‐amino acids. Enantiomers of these derivatives are efficiently separated on an amide‐derived chiral stationary phase. The chromatographic separations enable accurate determination of optical purity of the chiral β‐ lactams, prepared from homochiral ester enolate‐imine condensation. The absolute configuration of the major enantiomer of the β‐amino acid derivatives was determined from elution order on a chiral column.