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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 32, Number 4
BKCSDE 32(4)
April 20, 2011 

Enantioselective Recognition of Amino Alcohols and Amino Acids by Chiral Binol- Based Aldehydes with Conjugated Rings at the Hydrogen Bonding Donor Sites
Jiyoung Kim, Raju Nandhakumar,*, Kwan Mook Kim*,
Chiral aldehyde, Chirality conversion, Enantioselective imine formation, Amino alcohols, Amino acids
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.
1263 - 1267
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