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Remarkable enantioselectivity enhancement of the extractors with nonaxial chirality in liquid–liquid extraction of underivatized amino acids by introducing t-butyl group
- Title
- Remarkable enantioselectivity enhancement of the extractors with nonaxial chirality in liquid–liquid extraction of underivatized amino acids by introducing t-butyl group
- Authors
- Jin Y.; Chen Q.; Zhang Y.; Lee Y.; Kang D.; Kim Y.; Kim S.-J.; Su Z.; Huang H.; Kim K.M.
- Ewha Authors
- 김성진; 김영미; 김관묵
- SCOPUS Author ID
- 김성진; 김영미; 김관묵
- Issue Date
- 2022
- Journal Title
- Chirality
- ISSN
- 0899-0042
- Citation
- Chirality vol. 34, no. 7, pp. 999 - 1007
- Keywords
- amino acid; bulky imine; chiral extractor; liquid–liquid extraction
- Publisher
- John Wiley and Sons Inc
- Indexed
- SCIE; SCOPUS
- Document Type
- Article
- Abstract
- A class of carbonyl extractors, (R)-3, (R)-4, and (R)-5, with nonaxial chirality containing asymmetric carbons has been synthesized and studied for their efficiencies in enantioselective liquid–liquid extraction for underivatized amino acids. The bulky t-butyl ketone extractors, (R)-4 and (R)-5, showed the stereoselectivities ranging 5.4–9.4 of l/d ratio much better than those of the aldehyde extractor, (R)-3, ranging 2.4–5.2. The imine formation rates and yields of the t-butyl ketones were not significantly affected by their bulkiness and even in the absence of resonance-assisted hydrogen bond. This work confirms that a bulky t-butyl ketone can be a good choice in the development of an extractor not only with axial chirality but also with nonaxial chirality for the enantioselective extraction of unprotected amino acids. © 2022 Wiley Periodicals LLC.
- DOI
- 10.1002/chir.23449
- Appears in Collections:
- 자연과학대학 > 화학·나노과학전공 > Journal papers
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