The determination of the absolute configuration of a chiral molecular tweezer using CD spectroscopy

Tetrahedron Letters

Volumn 38, Issue 50, 1997, Pages 8655-8658

  Fleischhauer, Joerg ^a   Harmata, Michael ^b   Kahraman, Mehmet ^b   Koslowski, Axel ^a   Welch, Christopher J ^c  

^a RWTH AACHEN UNIVERSITY   (Germany)

^b UNIVERSITY OF MISSOURI   (United States)

^c REGIS TECHNOLOGIES INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC HYDROCARBON;

ARTICLE; CIRCULAR DICHROISM; DRUG STRUCTURE; ENANTIOMER; STEREOCHEMISTRY;

EID: 0030833068     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10379-3     Document Type: Article

References (18)

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3. Chromatographic analysis was performed using a Kratos ABI Spectoflow 400 pump, a Rheodyne Model 7010 injector fitted with a 10mL sample loop, a Kratos Spectroflow 783 variable wavelength absorbance monitor, and a Hewlett-Packard HP 3396 integrating recorder. Chromatographic conditions: column = (R,R) Whelk-O 1 (1 cm x 25 cm); mobile phase = 5%IPA/hexane; flow rate = 4 mL/ min; detection = UV 280 nm. A sample of racemic dibenzofuran cleft (10 mg) was dissolved in mobile phase (2 mL). Injection of progressively increasing volumes of this solution showed that baseline resolution could still be achieved with an injection size of 400 uL (2 mg) with a run time of about 8 min. Collected fractions from four injections of 400 uLwere pooled and assayed using a 4.6 mm × 25 cm analytical (R,R) Whelk-O column, revealing enantiopurity greater than 98% ee for both fractions.
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5. CD measurements were carried out under constant nitrogen flow at 25.1 °C in an AVIV Circular Dichroism Spectrometer (AVIV Associates, Model 62DS ) with a 450 watt suprasil Xenon lamp. Spectra were taken as a solution in methylene chloride (0.016M for the first eluted enantiomer and 0.025M for the second eluted enantiomer) using a 2 mm cuvette.
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