Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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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

  • Jung, Hye-In (Department of Chemistry and Nano Science (BK21), Ewha Womans University) ;
  • Nandhakumar, Raju (Department of Chemistry and Nano Science (BK21), Ewha Womans University) ;
  • Yoon, Hoe-Jin (Department of Chemistry and Nano Science (BK21), Ewha Womans University) ;
  • Lee, Sang-Gi (Department of Chemistry and Nano Science (BK21), Ewha Womans University) ;
  • Kim, Kwan-Mook (Department of Chemistry and Nano Science (BK21), Ewha Womans University)
  • Received : 2010.02.08
  • Accepted : 2010.03.10
  • Published : 2010.05.20
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Abstract

Novel $H_8$-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 ($K_R/K_S$ = 9.8 ~ 19.4) of 2b in imine formation with 1,2-amino alcohols are higher than those of 2a ($K_R/K_S$ = 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).

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References

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