Abstract
Two new methods for the determinatuion of the absolute configuration of methyl 4-methyl-6-(2-methylprop-1-enyl)cyclohexa-1,3-dienecarboxylate are proposed, and the configurations attributed previously to its (+)- and (–)-enantiometers are confirmed. Chiral methyl carboxylate is converted into the corresponding alcohol whose configuration is deduced from either the rate of hydrolysis of the respective racemic acetate in the presence of pancreatic lipase (method 1) or from the difference between the Eu(fod)3-induced shifts of the MeO signals in the 1H NMR spectra of the diastereomeric esters of S- or R-Mosher"s acid (method 2).
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Serebryakov, E.P., Shcherbakov, M.A., Gamalevich, G.D. et al. New ways to determine the absolute configurations of alkyl 6-R-cyclohexa-1,3-dienecarboxylates. Russian Chemical Bulletin 52, 734–739 (2003). https://doi.org/10.1023/A:1023987613185
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DOI: https://doi.org/10.1023/A:1023987613185