Chiral sensing by nonchiral tetrapyrroles

Accounts of Chemical Research
Jan LabutaKatsuhiko Ariga

Abstract

Enantiomeric excess (ee) is a measure of the purity of an enantiomer of a chiral compound with respect to the presence of the complementary enantiomer. It is an important aspect of chemistry, especially in the fields of pharmaceuticals and asymmetric catalysis. Existing methods for determination of enantiomeric excesses using nuclear magnetic resonance (NMR) spectroscopy mostly rely on special chiral reagents (auxiliaries) that form two or more diastereomeric complexes with a chiral compound. As a result of this, the NMR spectrum of each enantiomer is different, allowing the determination of enantiomeric excess. In this Account, we describe a molecular design process that has allowed us to prepare prochiral solvating agents for NMR determination of ee of a wide variety of analyte types. At the outset of this work, we initially encountered the phenomenon of NMR peak splitting in the oxoporphyrinogen (OxP) host component of a supramolecular host-guest complex, where the extent of the splitting is apparently proportional to the guests' ee. Upon closer examination of the mechanism of action, it was found that several complicating factors, including prototropic tautomerism, macrocyclic inversion (ring-flipping), and 1:2 host-guest s...Continue Reading

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Citations

Nov 20, 2015·The Journal of Organic Chemistry·Julia BuendiaLuis Sanchez
Oct 24, 2015·Photochemistry and Photobiology·Albish K PaulDanaboyina Ramaiah
Aug 9, 2016·The Journal of Organic Chemistry·Li WangSheryl L Wiskur
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Nov 15, 2016·Organic & Biomolecular Chemistry·Jennifer A MelansonAlison Thompson
Jul 7, 2017·Physical Chemistry Chemical Physics : PCCP·Katsuhiko ArigaJonathan P Hill
Mar 17, 2018·Chemical Communications : Chem Comm·Min-Seob SeoHyunwoo Kim
Feb 16, 2016·The Analyst·Katsuhiko ArigaLok Kumar Shrestha
Nov 2, 2016·Chemical Communications : Chem Comm·A Di MauroR Purrello
Jul 1, 2018·Chemistry, an Asian Journal·Joshua A JackmanKatsuhiko Ariga
Jul 30, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Mandeep K ChahalJonathan P Hill
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Feb 20, 2020·Accounts of Chemical Research·Jing LiuKatsuhiko Ariga

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