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Analytic and preparative resolution of recemic γ‐ and δ‐lactones by chromatography on cellulose triacetate. Relationship between elution order and absolute configuration
Author(s) -
Francotte Eric,
Lohmann Dieter
Publication year - 1987
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19870700615
Subject(s) - chemistry , cellulose triacetate , enantiomer , absolute configuration , elution , ring (chemistry) , cellulose , resolution (logic) , chromatography , stereochemistry , organic chemistry , artificial intelligence , computer science
Enantiomers of various chiral five‐ and six‐membered‐ring lactones, Which are important classes of compounds (flavour and Pheromone components, key intermediates in the synthesis of biologically active substances) have been separated chromatographically on the chiral phase cellulose triacetate, crystallographic form I (CTAI). For different series of five‐membered‐ring lactones, relationships have been found between the elution order of the enantiomers and their absolute configuration. Preparative resolutions of γ‐Phenyl‐γ‐butyrolactone ( 1 ) and of the Pheromone component 5b have been carried out to demonstrate the applicability of the method to g‐scale separations.