Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Enantioselective Recognition of Amino Alcohols and Amino Acids by Chiral Binol-Based Aldehydes with Conjugated Rings at the Hydrogen Bonding Donor Sites

  • Kim, Ji-Young (Bio-Chiral Lab, Department of Chemistry and Nano Sciences, Ewha Womans University) ;
  • Nandhakumar, Raju (Bio-Chiral Lab, Department of Chemistry and Nano Sciences, Ewha Womans University) ;
  • Kim, Kwan-Mook (Bio-Chiral Lab, Department of Chemistry and Nano Sciences, Ewha Womans University)
  • Received : 2011.01.29
  • Accepted : 2011.02.15
  • Published : 2011.04.20
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Abstract

Novel binol-based uryl and guanidinium receptors having higher ring conjugation at the periphery of the hydrogen bonding donor sites have been synthesized and utilized to study the enantioselective recognition of 1,2-aminoalcohols and chirality conversion of natural amino acids via imine bond formation. There is a remarkable decrease in the stereoselectivites as the conjugation increases at the periphery of hydrogen bonding donor sites. The guanidinium-based receptors show more selectivity towards the amino alcohol than that of the uryl based ones due to its charge reinforced hydrogen bonds. The conversion efficiency of L-amino acids to Damino acids by the uryl-based receptors is higher than that of the guanidinium-based ones.

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