Remarkable enantioselectivity enhancement of the extractors with nonaxial chirality in liquid–liquid extraction of underivatized amino acids by introducing t-butyl group

Yingji Jin, Qian Chen, Yan Zhang, Yejeong Lee, Dayoung Kang, Youngmee Kim, Sung Jin Kim, Zhishan Su, Haofei Huang, Kwan Mook Kim

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
JournalChirality
DOIs
StateAccepted/In press - 2022

Keywords

  • amino acid
  • bulky imine
  • chiral extractor
  • liquid–liquid extraction

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