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http://dx.doi.org/10.5012/bkcs.2011.32.4.1263

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)
Publication Information
Bulletin of the Korean Chemical Society / v.32, no.4, 2011 , pp. 1263-1267 More about this Journal
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.
Keywords
Chiral aldehyde; Chirality conversion; Enantioselective imine formation; Amino alcohols; Amino acids;
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