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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
Author(s) -
Hu Yulin,
Ziffer Herman
Publication year - 1991
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.530030310
Subject(s) - chemistry , enantiomer , elution , chromatography , high performance liquid chromatography , chiral column chromatography , diastereomer , chiral derivatizing agent , silica gel , absolute configuration , hydrolysis , stereochemistry , organic chemistry
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 γ‐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.