ISSN:
0899-0042
Keywords:
(R)-
;
(S)-1,2-benzocyclononen-3-ol
;
(R)-1,2-benzocyclodecen-3-ol
;
separation of enantiomers of Pirkle HPLC columns
;
chiral recognition
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/chir.530030310
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