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A new chiral selector based on trans-acenaphthen-1,2-dicarboxylic acid.
MedLine Citation:
PMID:  11143809     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
The chiral selectors (R,R)- and (S,S)-trans-acenaphthen-1,2-dicarboxylic acid bis-allylamide have been synthesized and characterized. The route to the selectors involved synthesis of the trans-dicarboxylic acid via sodiation and carbonation of acenaphthylene, followed by reaction of the bis-acid chloride with allylamine. The racemic bis-allylamide derivative was resolved into its enantiomers by preparative liquid chromatography. The chiral discrimination effect from the (R,R)-selector in the 1H-NMR spectra of a mixture of the enantiomers of O,O'-dibenzoyltartaric acid was studied as a function of temperature. Due to certain ambiguities in the literature concerning the absolute configuration of the (+)-rotating trans-acenaphthen-1,2-dicarboxylic acid, its brucine salt was subjected to X-ray crystallography. This showed the (+)-form to be of (R,R)-configuration.
Authors:
S Allenmark; U Skogsberg
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Enantiomer     Volume:  5     ISSN:  1024-2430     ISO Abbreviation:  Enantiomer     Publication Date:  2000  
Date Detail:
Created Date:  2000-12-15     Completed Date:  2002-10-01     Revised Date:  2003-10-31    
Medline Journal Info:
Nlm Unique ID:  9612491     Medline TA:  Enantiomer     Country:  England    
Other Details:
Languages:  eng     Pagination:  451-5     Citation Subset:  -    
Affiliation:
Department of Chemistry, University of Göteborg, SE-41296 Göteborg, Sweden. stig.allenmark@oc.chalmers.se
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