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.