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Synthesis of novel H8-binaphthol-based chiral receptors and their applications in enantioselective recognition of 1,2-amino alcohols and chirality conversion of L-amino acids to D-amino acids

Title
Synthesis of novel H8-binaphthol-based chiral receptors and their applications in enantioselective recognition of 1,2-amino alcohols and chirality conversion of L-amino acids to D-amino acids
Authors
Jung H.Nandhakumar R.Yoon H.J.Lee S.G.Kim K.M.
Ewha Authors
김관묵이상기
SCOPUS Author ID
김관묵scopus; 이상기scopus
Issue Date
2010
Journal Title
Bulletin of the Korean Chemical Society
ISSN
0253-2964JCR Link
Citation
vol. 31, no. 5, pp. 1289 - 1294
Indexed
SCI; SCIE; SCOPUS; KCI WOS scopus
Abstract
Novel H8-binaphthol-based chiral receptors appended with an uryl moiety (2a) and a guanidinium moiety (2b) have been designed and synthesized for the enantioselective recognition of 1,2-amino alcohols via reversible imine formation. The selectivities (KR/KS = 9.8 ̃ 19.4) of 2b in imine formation with 1,2-amino alcohols are higher than those of 2a (KR/KS = 1.8 ̃ 4.5). Similar efficiency trend have been observed in the conversion of L-amino acids to D-amino acids, i.e., the efficiency of the receptor 2b (D/L ratio: 4.3 ̃ 10.1) is superior to 2a (D/L ratio: 4.0 ̃ 8.7).
DOI
10.5012/bkcs.2010.31.5.1289
Appears in Collections:
자연과학대학 > 화학·나노과학전공 > Journal papers
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