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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
- 김관묵
- Issue Date
- 2015
- Journal Title
- Bulletin of the Korean Chemical Society
- ISSN
- 0253-2964
- Citation
- Bulletin of the Korean Chemical Society vol. 36, no. 7, pp. 1834 - 1837
- Keywords
- Chiral imine; Enantioselective extractor; Optical resolution
- Publisher
- Korean Chemical Society
- Indexed
- SCI; SCIE; SCOPUS; KCI
- Document Type
- Article
- 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
- Appears in Collections:
- 자연과학대학 > 화학·나노과학전공 > Journal papers
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