Recent Advances in the Application of Vibrational Circular Dichroism Spectroscopy for the Characterization of Asymmetric Catalysts

In this Minireview, we summarize our recent efforts to use vibrational circular dichroism (VCD) spectroscopy, the chiroptical version of IR spectroscopy, for the characterization of conformational preferences of asymmetric catalysts and complexes, formed upon the respective interactions or reactions...

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Bibliographic Details
Published in:European journal of organic chemistry 2020-10, Vol.2020 (37), p.5892-5900
Main Author: Merten, Christian
Format: Article
Language:English
Subjects:
Asymmetric catalysis
Asymmetry
Catalysts
Chirality
Computational chemistry
Dichroism
Enantiomers
Hydrogen bonding
Infrared spectroscopy
Reaction mechanisms
Spectrum analysis
Substrates
Vibrational spectroscopy
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Summary:In this Minireview, we summarize our recent efforts to use vibrational circular dichroism (VCD) spectroscopy, the chiroptical version of IR spectroscopy, for the characterization of conformational preferences of asymmetric catalysts and complexes, formed upon the respective interactions or reactions of catalysts with substrates. After giving a brief overview of the general aspects of the technique, we showcase how VCD spectra of a chiral ion‐pairing catalyst could be used to confirm a conformational shifting mechanism that determines the enantioselectivity of the catalyst. Chiral thioureas serve as examples for hydrogen bonding organocatalysts for which we demonstrate that both conformational preferences of the catalysts as well as of the hydrogen‐bonded complexes with substrates can be obtained from a detailed computational spectra analysis. Jørgensen–Hayashi‐type prolinol ether catalysts serve as examples to introduce experimental challenges associated with catalysts that operate by covalent activation of reactants. Vibrational circular dichroism (VCD) spectroscopy, the chiroptical version of IR spectroscopy, is introduced as powerful a tool for the characterization of conformational preferences of asymmetric catalysts, catalyst‐reactant complexes, and activated species. Examples from ion‐pairing catalysis, hydrogen‐bonding organocatalysis, and enamine chemistry demonstrate that the computational analysis of VCD spectra can give deep insights into structural preferences of catalytically relevant species.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202000876