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
✍ Scribed by Yulin Hu; Herman Ziffer
- Publisher
- John Wiley and Sons
- Year
- 1991
- Tongue
- English
- Weight
- 697 KB
- Volume
- 3
- Category
- Article
- ISSN
- 0899-0042
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✦ Synopsis
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.