Supramolecular method for the determination of absolute configuration of chiral compounds: theoretical derivatization and a demonstration for a phenolic crown ether-2-amino-1-ethanol system.
A combination of anisotropic shielding effect and temperature dependence of NMR chemical shifts makes it possible to develop a supramolecular method for determination of absolute configuration of chiral compounds. The concept, theoretical derivatization, and first demonstration of this daedal noncovalent method using a host-guest system is described. This noncovalent method requires only three substrate solutions and can in principle be applied to any host-guest systems that follow the van't Hoff relation and have a clear anisotropic shielding effect based on a well-defined complex structure regardless of the extent of enantiomer selectivity.
Hirose
Keiji
K
Division of Frontier Materials Science, Graduate School of Engineering Science, Osaka University, 1-3 Machikaneyama, Toyonaka, Osaka 560-8531, Japan. hirose@chem.es.osaka-u.ac.jp
Goshima
Yoko
Y
Wakebe
Takanori
T
Tobe
Yoshito
Y
Naemura
Koichiro
K
D043844:Crown Ethers / Q000737:chemistry*; D004983:Ethanolamines / Q000737:chemistry*; D008722:Methods; D015394:Molecular Structure; D013237:Stereoisomerism
D043844:Crown Ethers; D004983:Ethanolamines