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DOI: 10.1055/s-2001-16767
Asymmetric Catalysis; 138: [1] Synthesis of Enantiomerically Pure 2-Pyridinyl-α-ethanols via Diastereomeric Camphanic Esters
Publication History
Publication Date:
28 September 2004 (online)
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Abstract
New terdentate facially binding ligands based on the 2-pyridinyl-α-ethanol skeleton were prepared as the racemates. Reaction with the enantiomerically pure (-)-(1S,4R)-camphanoyl chloride gave diastereomeric camphanic esters. The pure diastereomers were accessible by separating the diastereomeric esters with medium-pressure silica gel chromatography or fractional crystallization. X-ray structure analysis of the pure camphanic esters established the absolute configurations of the 2-pyridinyl-α-alcohols. The enantiomerically pure alcohols were obtained after saponification of the diastereomerically pure esters.
Key words
facial coordination - terdentate ligands - chiral 2-pyridinyl-α-alcohols - absolute configuration
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References
X-ray structure analyses.
10Crystallographic data (excluding structure factors)for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC 162515 [for (±)-3], CCDC 162518 [for (±)-5], CCDC 162514 [for(diphenylphosphanyl)methyl-2-pyridinylketone], CCDC 162512 [for(phenylsulfanyl)methyl-2-pyridinylketone], CCDC 162513 [for (2S,4S)-2-(2-pyridinyl)-4-carboethoxy-1,3-thiazolidine: BESTHIA], CCDC 162516 [for (S)-(-)-9], CCDC 162520 [for (R)-(-)-11], CCDC 162517 [for (S)-(+)-12] and CCDC 162519 [for (R)-(-)-13]. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk).