Remarkable enantioselectivity enhancement of the extractors with nonaxial chirality in liquid–liquid extraction of underivatized amino acids by introducing t-butyl group
- 주제(키워드) amino acid , bulky imine , chiral extractor , liquid–liquid extraction
- 등재 SCIE, SCOPUS
- 발행기관 John Wiley and Sons Inc
- 발행년도 2022
- 총서유형 Journal
- URI http://www.dcollection.net/handler/ewha/000000193079
- 본문언어 영어
- Published As https://doi.org/10.1002/chir.23449
- PubMed https://pubmed.ncbi.nlm.nih.gov/35417058
초록/요약
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.
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