The syntheses of five optically active α-aryl-2-pyridylmethanols 1–5 are described. It is shown by means of chemical correlation with the known (−)-(αR,2S)-α-phenyl-2-piperidylmethanol 6 that all levo-rotatory isomers of 1–4 are of R configuration. It is also found via the relative integral intensities in the infrared spectra of the bands due to free and intramolecularly bonded hydroxyl groups in the compounds 1–4 and the free hydroxyl groups in the model compounds 7–10, that the population of the conformers with an intramolecular OH···N bond in compounds 1–4 exceeds 80%.
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ChemInform Abstract Racemic title carbinols are synthesized as described in the scheme and resolved by standard procedures using (+)-camphor-10-sulfonic acid or (-)-tartaric acid. The optically active carbinols, e.g. (I) and (II), form complexes with Mo2(O-Ac)4. The CD-spectra of complexes with (R)-configurated carbinols have negative CD-bands between 408-470 nm and show a positive Cotton effect between 335-380 nm.
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