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Enantiomeric separation of cyclopropane derivatives on a polysaccharide-based chiral stationary phase


Ghanem, A and Hoenen, H and Muller, P and Aboul-Enein, HY, Enantiomeric separation of cyclopropane derivatives on a polysaccharide-based chiral stationary phase, Analytica Chimica Acta, 538, (1-2) pp. 15-24. ISSN 0003-2670 (2005) [Refereed Article]

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DOI: doi:10.1016/j.aca.2005.02.038


The enantioseparation of a set of new cyclopropanes derived from Meldrum's acid, dimethyl malonate, (silanoxyvinyl)-diazoacetates and 3,3,3-trifluoro-2-diazopropionate has been achieved on cellulose tris(3,5-dimethylphenylcarbamate) Chiralcel OD coated on 10 ìm silica-gel as chiral stationary phase in high-performance liquid chromatography (HPLC). The HPLC was equipped with a sensitive optical rotation detector for monitoring the optical activity of the racemic and enantioenriched cyclopropanes prepared via the Rh(II)-catalyzed asymmetric intermolecular cyclopropanations. The mobile phase was a mixture of n-hexane-2-propanol (90:10, or 99:1, v/v) with a flow-rate of 0.3 ml/min. The UV detector was set at 254 nm. The advantages of the liquid over the gas chromatographic analysis of the cyclopropanes are demonstrated by a comparative study of both methods. The methods provide an easy and direct determination of the enantiomeric excesses of the cyclopropanes.

Item Details

Item Type:Refereed Article
Keywords:Cellulose tris(3,5-dimethylphenylcarbamate); Cyclopropanes; Enantiomeric excess; Enantioseparation; HPLC; Polysaccharide chiral stationary phase; Rhodium complexes
Research Division:Chemical Sciences
Research Group:Analytical chemistry
Research Field:Separation science
Objective Division:Expanding Knowledge
Objective Group:Expanding knowledge
Objective Field:Expanding knowledge in the chemical sciences
UTAS Author:Ghanem, A (Dr Ashraf Ghanem)
ID Code:58314
Year Published:2005
Web of Science® Times Cited:6
Deposited By:Austn Centre for Research in Separation Science
Deposited On:2009-09-25
Last Modified:2009-09-25

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