Enantioselective recognition of amino alcohols and amino acids by chiral binol-based aldehydes with conjugated rings at the hydrogen bonding donor sites
Title
Enantioselective recognition of amino alcohols and amino acids by chiral binol-based aldehydes with conjugated rings at the hydrogen bonding donor sites
Bulletin of the Korean Chemical Society vol. 32, no. 4, pp. 1263 - 1267
Indexed
SCI; SCIE; SCOPUS; KCI
Document Type
Article
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.