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

doi:10.1021/ac070217c

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

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	6295-6302
Number of pages	8
Journal	Analytical Chemistry
Volume	79
Issue number	16
DOIs	https://doi.org/10.1021/ac070217c
State	Published - 15 Aug 2007

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title = "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",

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.",

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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. / Hirose, Keiji; Goshima, Yoko; Wakebe, Takanori; Yoshito, Tobe; Naemura, Koichiro.

In: Analytical Chemistry, Vol. 79, No. 16, 15.08.2007, p. 6295-6302.

Research output: Contribution to journal › Article › peer-review

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AU - Yoshito, Tobe

AU - Naemura, Koichiro

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