Determining Enantiomeric Excess Utilizing Ratiometric Measurements of a Deuterium Labeled Malonate By ¹H NMR Spectroscopy

Authors

Thomas A. Owens, University of Southern Mississippi
Anna Chataginer, University of Southern Mississippi
Robert J. Wehrle, University of Southern MississippiFollow
Douglas S. Masterson, University of Southern MississippiFollow

Document Type

Article

Publication Date

1-31-2024

Department

Chemistry and Biochemistry

School

Mathematics and Natural Sciences

Abstract

Enantiomeric excess quantification is important in the synthesis of many small molecules. Esterase enzymes such as porcine liver esterase are known for their ability to generate high enantioselectivity. Many methods have been developed in order to measure the enantiomeric excess of a chiral mixture. Herein we report a new method of direct quantification by ¹H NMR spectroscopy of an enantiomeric mixture using ratiometric measurements of an isotope labelled probe. Our method has been demonstrated to be comparable to that of HPLC and yield quantitative results with ease.

Publication Title

Tetrahedron Letters

Volume

135

Recommended Citation

Owens, T. A., Chataginer, A., Wehrle, R. J., Masterson, D. S. (2024). Determining Enantiomeric Excess Utilizing Ratiometric Measurements of a Deuterium Labeled Malonate By ¹H NMR Spectroscopy. Tetrahedron Letters, 135.
Available at: https://aquila.usm.edu/fac_pubs/21586