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Efficient synthesis of chiral binaphthol aldehyde with phenyl ether linkage for enantioselective extraction of amino acids
- Efficient synthesis of chiral binaphthol aldehyde with phenyl ether linkage for enantioselective extraction of amino acids
- Choi M.; Jun M.-J.; Kim K.M.
- Ewha Authors
- SCOPUS Author ID
- Issue Date
- Journal Title
- Bulletin of the Korean Chemical Society
- vol. 36, no. 7, pp. 1834 - 1837
- Chiral imine; Enantioselective extractor; Optical resolution
- Korean Chemical Society
- SCI; SCIE; SCOPUS; KCI
- A binaphthol aldehyde with phenyl ether linkage, compound 2, has been synthesized starting from binaphthol-3-carboxylic acid. The axially chiral binaphthol ring was racemized during the synthesis due to high temperatures required in O-phenylation reaction. The enantiomerically pure form of 2 was obtained from the resolution of the diastereomeric imine of 2. Optically pure compound (S)-2 was applied to the enantioselective liquid-liquid extraction of amino acid between CH<inf>2</inf>Cl<inf>2</inf> and aqueous layers.The stereoselectivities, that is, D/L ratio of the amino acid extracted, ranged from 3.57 to 11.1. One carbon was absent in compound (S)-2 compared to the compound (S)-1 with benzyl ether linkage, which differentiated the conformations of their imines formed with amino acids. © 2015 Korean Chemical Society, Seoul & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
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