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

Keiji Hirose*, Yoko Goshima, Takanori Wakebe, Tobe Yoshito, Koichiro Naemura

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)6295-6302
Number of pages8
JournalAnalytical Chemistry
Volume79
Issue number16
DOIs
StatePublished - 15 Aug 2007

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