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Published on: November 7, 2018
Enantioselective high-performance liquid chromatography combined with spectroscopic methods and theoretical
Simone Manetto1, Giulia Mazzoccanti1, Gaia Pulitelli2
1Department of Drug Chemistry and Technology, "Sapienza" University of Rome, Rome, Italy.
Abstract:
The absolute configuration of three chiral eugenol derivatives was assigned by a multi-step methodology based on enantioselective HPLC combined with spectroscopic and theoretical calculations. Milligram amounts of enantiopure forms used for stereochemical characterization were isolated by HPLC on the immobilized amylose-based chiral stationary phase Chiralpak IG using normal phase elution conditions. The absolute configuration was indirectly determined for one of the three compounds by 1H NMR via methoxy-α-trifluoromethyl-α-phenylacetic acid derivatization (Mosher's acid). Comparison of the experimental and predicted electronic circular dichroism spectra confirmed the stereochemical assignment by Mosher's method and extended the absolute configuration assignment to two other chiral compounds.
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