Lanthanide Enolates as Nuclear Magnetic Resonance Shift Reagents

Wenzel, Thomas J.; Provencher, Katelyn A.

doi:10.1002/9780470682531.pat0430

Patai's Chemistry of Functional Groups 2010

DOI: 10.1002/9780470682531.pat0430

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Lanthanide Enolates as Nuclear Magnetic Resonance Shift Reagents

Thomas J. Wenzel

Katelyn A. Provencher

Abstract: Introduction General Considerations Applications of Achiral Shift Reagents Coupling of Achiral Shift Reagents to Chiral Derivatizing and Solvating Agents Chiral Shift Reagents Binuclear Lanthanide–Silver Shift Reagents

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2013

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Chiral Derivatizing Agents, Macrocycles, Metal Complexes, and Liquid Crystals for Enantiomer Differentiation in NMR Spectroscopy

Wenzel

2013

Topics in Current Chemistry

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Enantiomerically pure chiral auxiliary agents are often used in NMR spectroscopy to facilitate the differentiation of enantiomers. Chiral derivatizing agents are covalently bound to the substrate and differences in chemical shifts of the resulting diastereomeric complexes are used in the analysis. Macrocycles such as cyclodextrins, crown ethers, and calix[4]resorcinarenes are chiral solvating agents that associate with the substrate through non-covalent interactions. Enantiomeric differentiation occurs in the NMR spectrum because of the diastereomeric nature of the associated complexes and/or because of the differences in association constants between the two enantiomers and the chiral reagent. Metal complexes are Lewis acids that bind to suitable Lewis base donor compounds. Exchange of substrate can be slow or fast depending on the particular metal ion, mimicking the behavior of a chiral derivatizing or solvating agent, respectively. Chiral liquid crystals undergo a partial alignment in an applied magnetic field and enantiomers dissolved in the liquid crystal undergo a partial alignment as well. If the alignment of the two enantiomers is different, enantiomeric differentiation can potentially be observed by differences in chemical shifts, differences in dipolar coupling constants, and different magnitudes of splitting of quadrupolar nuclei such as deuterium. The chiral reagents described herein can be used to determine enantiomeric composition and sometimes to assign absolute configuration. Significant discoveries as well as recent findings with each of these types of systems are described.

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Chiral Derivatizing Agents, Macrocycles, Metal Complexes, and Liquid Crystals for Enantiomer Differentiation in NMR Spectroscopy

Wenzel

2013

Topics in Current Chemistry

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Lanthanide Enolates as Nuclear Magnetic Resonance Shift Reagents

Abstract: Introduction General Considerations Applications of Achiral Shift Reagents Coupling of Achiral Shift Reagents to Chiral Derivatizing and Solvating Agents Chiral Shift Reagents Binuclear Lanthanide–Silver Shift Reagents

Cited by 1 publication

References 194 publications

Chiral Derivatizing Agents, Macrocycles, Metal Complexes, and Liquid Crystals for Enantiomer Differentiation in NMR Spectroscopy

Chiral Derivatizing Agents, Macrocycles, Metal Complexes, and Liquid Crystals for Enantiomer Differentiation in NMR Spectroscopy

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