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Efficient synthesis of chiral binaphthol aldehyde with phenyl ether linkage for enantioselective extraction of amino acids

Title
Efficient synthesis of chiral binaphthol aldehyde with phenyl ether linkage for enantioselective extraction of amino acids
Authors
Choi M.Jun M.-J.Kim K.M.
Ewha Authors
김관묵
SCOPUS Author ID
김관묵scopus
Issue Date
2015
Journal Title
Bulletin of the Korean Chemical Society
ISSN
0253-2964JCR Link
Citation
vol. 36, no. 7, pp. 1834 - 1837
Keywords
Chiral imineEnantioselective extractorOptical resolution
Publisher
Korean Chemical Society
Indexed
SCI; SCIE; SCOPUS; KCI WOS scopus
Abstract
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.
DOI
10.1002/bkcs.10354
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자연과학대학 > 화학·나노과학전공 > Journal papers
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