31P NMR parameters may facilitate the stereochemical analysis of phosphorus-containing compounds

Conventional Nuclear Magnetic Resonance (NMR) analysis relies on H-H/C-H interactions. However, these interactions are sometimes insufficient for an accurate and precise NMR analysis. In this study, we show that P-31 NMR parameters can provide critical structural insights into the stereochemistry of phosphorus-containing compounds. For this purpose, we prepared a set of model phosphorus-based pro-line derivatives, separated diastereoisomers, and determined their absolute configuration by single-crystal X-ray diffraction. After supplementing these results by electronic circular dichroism (ECD) spec-troscopy, we combined experimental data and DFT calculations from our model compounds to perform a detailed conformational analysis, thereby determining their relative configuration. Overall, our findings establish an experimental paradigm for combining P-31 NMR spectroscopy with other optical methods to facilitate the stereochemical analysis of phosphorus-containing compounds.(C) 2022 Elsevier Inc. All rights reserved.