A new model to account for the order in which enantiomers of alkylarylcarbinols elute from a Pirkle chiral HPLC column: preparation, absolute stereochemistry, and chromatographic properties of (+)-1,2-benzocyclononen-3-ol and (+)-1,2-benzocyclodecen-3-ol.
Samples enriched in (-)- and (+)-1,2-benzocyclononen-3-ol were prepared by microbially mediated reactions. An enriched sample of (+)-1,2-benzocyclodecen-3-ol was prepared by fractional crystallization of the diastereoisomeric camphanates, followed by hydrolysis. The absolute stereochemistry of both alcohols was established by chemical transformations. The elution order of their enantiomers from a chiral Pirkle HPLC column [(R)-N-(3,5-dinitrobenzoyl)phenyl glycine ionically bound to gamma-aminopropyl silanized silica] was determined. The information in conjunction with other data was used to formulate a rule to predict the configuration of an enantiomer of an alkylarylcarbinol from its elution order from this column.
Hu
Y L
YL
Laboratory of Chemical Physics, NIDDK, National Institutes of Health, Bethesda, Maryland 20892.
Ziffer
H
H
D002851:Chromatography, High Pressure Liquid; D008956:Models, Chemical; D008968:Molecular Conformation; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification*; D013237:Stereoisomerism
D011083:Polycyclic Compounds; C071122:1,2-benzocyclononen-3-ol; C071121:1,2-benzocyclodecen-3-ol