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Comparison of CD Spectra of (2-Methylphenyl)- and (2,6-Dimethylphenyl)-phenylmethanols Leads to Erroneous Absolute Configurations
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2002
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EngineeringR Absolute ConfigurationOrganic ChemistryComputational ChemistryChemistryHeterocycle ChemistrySpectra-structure CorrelationLinear Chain CompoundStructure ElucidationStereoselective SynthesisAbsolute ConfigurationBiochemistryQuantum ChemistryEnantioselective SynthesisBiomolecular EngineeringCd SpectraNatural SciencesAlcohols 2Erroneous Absolute ConfigurationsSynthetic Chemistry
Enantiopure (2,6-dimethylphenyl)phenylmethanol (+)-(3) and analog (+)-(4) were prepared and their CD spectra were found opposite to that of (2-methylphenyl)phenylmethanol (R)-(-)-(2), the absolute configuration of which was previously established by X-ray crystallography. Therefore the S absolute configuration was once assigned to (+)-3 and (+)-4. After that we have succeeded in the X-ray analyses of chiral dichlorophthalate esters of (+)-3 and (+)4, which clearly indicated R absolute configuration. It is thus evident that comparison of the CD spectra of alcohols 2, 3, and 4 leads to erroneous absolute configurations.